Updated on 2026/07/30

写真a

 
URABE Daisuke
 
Organization
Graduate School of Bioagricultural Sciences Department of Applied Biosciences Professor
Title
Professor
Contact information
メールアドレス
External link

Degree 1

  1. 博士(農学) ( 2006.3   名古屋大学 ) 

Research Interests 4

  1. Theoretical Chemistry

  2. Computational Chemistry

  3. Natural Product Synthesis

  4. Natural Product Chemistry

Research Areas 1

  1. Life Science / Bioorganic chemistry

Current Research Project and SDGs 4

  1. Structural Study of Natural Products

  2. Theoretical Study of Organic Reactions

  3. Design and Synthesis of Antibiotics

  4. Synthetic Study of Bioactive Natural Products

Research History 7

  1. Nagoya University   Graduate School of Bioagricultural Sciences Department of Applied Biosciences   Professor

    2026.6

  2. Toyama Prefectural University   Professor

    2017.4 - 2026.5

  3. The University of Tokyo   Lecturer

    2013.10 - 2017.3

  4. The University of Tokyo   Assistant Professor

    2011.2 - 2013.9

  5. The University of Tokyo   Assistant Professor

    2008.1 - 2011.1

  6. Harvard University   Department of Chemistry and Chemical Biology

    2006.5 - 2007.12

  7. ハーバード大学   化学生物化学科   博士研究員

    2006.5 - 2007.12

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Education 3

  1. Nagoya University   Graduate School of Bioagricultural Sciences

    2003.4 - 2006.3

  2. Nagoya University   Graduate School of Bioagricultural Sciences

    2001.4 - 2003.3

  3. Nagoya University   School of Agricultural Scineces

    1997.4 - 2001.3

Professional Memberships 4

  1. 日本化学会

  2. 有機合成化学協会

  3. 日本薬学会

  4. 日本農芸化学会

Awards 3

  1. 日本薬学会奨励賞

    2015.3  

  2. Thieme Chemistry Journal Award

    2014.1  

  3. 第48回天然物化学談話会奨励賞

    2013.7  

 

Papers 107

  1. Initial Stage of Guaiacyl-Syringyl Lignin Formation from Coniferyl and Sinapyl Alcohols Reviewed

    Yamaguchi, A; Senda, K; Urabe, D; Kishimoto, T

    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY   Vol. 74 ( 23 ) page: 18099 - 18107   2026.6

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.jafc.6c05890

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  2. Synthesis of the decalin structure of cladoic acid Reviewed

    Kasashima, A; Rana, MM; Matoba, T; Kurihashi, C; Osaka, I; Fukaya, K; Urabe, D

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   Vol. 90 ( 1 ) page: 10 - 16   2026.1

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1093/bbb/zbaf154

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  3. Total Synthesis of Racemic Benzosceptrins via an Electrocyclization Cascade Reviewed

    Fujino, Y; Matoba, T; Amano, A; Saito, K; Fukuyama, K; Fukaya, K; Urabe, D

    ORGANIC LETTERS   Vol. 27 ( 49 ) page: 13456 - 13462   2025.12

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.orglett.5c04155

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  4. Synthesis of Unnatural Aplysiatoxin Analogs with High Affinity for Protein Kinase C Reviewed Open Access

    Morishita, M; Hada, K; Araki, Y; Fukaya, K; Urabe, D; Yanagita, RC; Maki, J; Hanaki, Y; Kita, M; Irie, K; Nishikawa, T

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   Vol. 28 ( 42 )   2025.11

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/ejoc.202500890

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  5. Synthesis of farinomaleins and their antimicrobial activities Reviewed

    Rana, MM; Oshima, T; Horiuchi, E; Osaka, I; Igarashi, Y; Urabe, D

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   Vol. 89 ( 11 ) page: 1557 - 1562   2025.11

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1093/bbb/zbaf125

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  6. Automated Reactivity Prediction of Complex Molecules and Its Application to Total Synthesis of Ageliferin Reviewed

    Fujino, Y; Fukaya, K; Urabe, D

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 147 ( 38 ) page: 34556 - 34563   2025.9

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/jacs.5c09045

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  7. Computationally Designed Dearomative Claisen-Type Rearrangement of a Benzyl Alkynyl Ether and Cascade Reaction To Provide a Dihydroindenone Reviewed

    Fukaya, K; Tanaka, K; Karashimada, R; Urabe, D

    ORGANIC LETTERS   Vol. 27 ( 36 ) page: 9867 - 9872   2025.9

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.orglett.5c02164

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  8. Synthesis of the Tricyclic ABC-Ring System of Veratridine Reviewed Open Access

    Shiono Keita, Fukaya Keisuke, Amano Ayami, Urabe Daisuke

    Chemical and Pharmaceutical Bulletin   Vol. 73 ( 5 ) page: 491 - 496   2025.5

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)   Publisher:The Pharmaceutical Society of Japan  

    <p>Veratridine is a neurotoxic compound classified into the cevanine group of the Veratrum alkaloids and is characterized by its highly functionalized hexacyclic structure. Here, we report the synthesis of the ABC-ring system of veratridine from a known <i>cis</i>-decalin. The <i>cis</i>-decalin was synthesized from 1,5-pentanediol by modification of a literature method. A site-selective acylation of the C3-hydroxy group with 3,4-dimethoxybenzoyl chloride, a chemo- and stereoselective (allyl)<sub>2</sub>Zn-mediated C9-allylation, and ring closing metathesis were employed as key transformations to construct the ABC-ring system of veratridine.</p>

    DOI: 10.1248/cpb.c25-00156

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    CiNii Research

  9. The Heat-Shock Metabolite Streptolactam D, Produced by High-Temperature Culture of <i>Streptomyces</i> sp. JA74, Promotes Thermotolerance via Self-Membrane Stabilization Reviewed Open Access

    Saito, S; Okumura, Y; Kataoka, S; Fukaya, K; Urabe, D; Arai, MA

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 147 ( 18 ) page: 15676 - 15685   2025.4

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/jacs.5c03026

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  10. Conjugate Position of Glucuronide and Sulfate in Piceatannol Derivatives Affects the Stability and Hydrolytic Resistance of the Conjugate in Biological Matrices Reviewed

    Nishikawa, M; Nakayama, M; Fukaya, K; Urabe, D; Ikushiro, S

    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY   Vol. 73 ( 1 ) page: 495 - 506   2025.1

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    DOI: 10.1021/acs.jafc.4c08072

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  11. <i>Aspergillus terreus</i> IFM 65899-THP-1 cells interaction triggers production of the natural product butyrolactone Ia, an immune suppressive compound Reviewed Open Access

    Ujie, Y; Saito, S; Fukaya, K; Urabe, D; Yaguchi, T; Arai, MA

    SCIENTIFIC REPORTS   Vol. 14 ( 1 )   2024.11

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1038/s41598-024-79837-7

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  12. Cladoic Acid, an Anti-<i>Trypanosoma cruzi</i> Polyketide from <i>Cladosporium</i> sp. TP-F2020 Reviewed International coauthorship

    Rana, MM; Lu, SY; Menjívar, TA; Fukaya, K; Nakajima-Shimada, J; Urabe, D; Igarashi, Y

    JOURNAL OF NATURAL PRODUCTS   Vol. 87 ( 8 ) page: 2126 - 2131   2024.8

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.jnatprod.4c00567

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  13. Synthesis of Macrolactone Core of <i>ent</i>-Formosalide A via Regioselective Ether Cyclization Reviewed

    Mozumi, R; Fukaya, K; Ito, H; Komatsu, T; Urabe, D

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 89 ( 11 ) page: 7991 - 8004   2024.5

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.joc.4c00633

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  14. Theoretical Analysis of Multi- conformational Transition States and Diastereo/Regio- selective Reactions in Natural Product Synthesis Invited Reviewed

    Urabe, D; Fukaya, K

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   Vol. 82 ( 11 ) page: 1079 - 1087   2024

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  15. Formal Total Synthesis of Batrachotoxin Enabled by Radical and Weix Coupling Reactions Reviewed

    Watanabe, Y; Sakata, K; Urabe, D; Hagiwara, K; Inoue, M

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 88 ( 24 ) page: 17479 - 17484   2023.12

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    Language:Japanese   Publishing type:Research paper (international conference proceedings)  

    DOI: 10.1021/acs.joc.3c02290

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  16. Initial Stage of Syringyl Lignin Formation from Sinapyl Alcohol Reviewed

    Yamaguchi, A; Kishimoto, T; Urabe, D

    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY   Vol. 71 ( 40 ) page: 14666 - 14677   2023.9

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    Authorship:Last author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.jafc.3c03402

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  17. Computational Study Focusing on a Comprehensive Conformational Analysis of Transition States for Aza-Spiro Ring Formations with N-Alkoxyamides Reviewed

    Fukaya, K; Sato, T; Chida, N; Urabe, D

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 88 ( 19 ) page: 13655 - 13665   2023.9

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    Authorship:Last author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.joc.3c01343

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  18. Isolation and structure determination of allopteridic acids A-C and allokutzmicin from an unexplored actinomycete of the genus <i>Allokutzneria</i> Reviewed

    Liu, C; Zhang, ZW; Fukaya, K; Oku, N; Harunari, E; Urabe, D; Igarashi, Y

    JOURNAL OF ANTIBIOTICS   Vol. 76 ( 6 ) page: 305 - 315   2023.6

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1038/s41429-023-00611-4

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  19. Species-specific secondary metabolism by actinomycetes of the genus <i>Phytohabitans</i> and discovery of new pyranonaphthoquinones and isatin derivatives Reviewed

    Triningsih, DW; Harunari, E; Fukaya, K; Oku, N; Urabe, D; Igarashi, Y

    JOURNAL OF ANTIBIOTICS   Vol. 76 ( 5 ) page: 249 - 259   2023.5

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    DOI: 10.1038/s41429-023-00605-2

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  20. Total Synthesis and Anti-inflammatory Activity of Stemoamide-Type Alkaloids Including Totally Substituted Butenolides and Pyrroles Reviewed

    Soda, Y; Sugiyama, Y; Sato, S; Shibuya, K; Saegusa, J; Matagawa, T; Kawano, S; Yoritate, M; Fukaya, K; Urabe, D; Oishi, T; Mori, K; Simizu, S; Chida, N; Sato, T

    SYNTHESIS-STUTTGART   Vol. 55 ( 04 ) page: 617 - 636   2023.2

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    Language:Japanese   Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/a-1941-8680

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  21. Krasilnikolides A and B and Detalosylkrasilnikolide A, Cytotoxic 20-Membered Macrolides from the Genus Krasilnikovia: Assignment of Anomeric Configuration by J-Based Configuration Analysis Reviewed

    Lu, SY; Zhou, T; Fukaya, K; Harunari, E; Oku, N; Urabe, D; Igarashi, Y

    JOURNAL OF NATURAL PRODUCTS   Vol. 85 ( 12 ) page: 2796 - 2803   2022.12

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.jnatprod.2c00781

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  22. Collective Synthesis of Aplysiatoxin/Oscillatoxin Analogues by a Bioinspired Strategy Reviewed

    Hada, K; Araki, Y; Nokura, Y; Urabe, D; Nishikawa, T

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 87 ( 22 ) page: 15618 - 15633   2022.11

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    DOI: 10.1021/acs.joc.2c02204

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  23. Cyclic enaminones and a 4-quinazolinone from an unidentified actinomycete of the family <i>Micromonosporaceae</i> Reviewed

    Triningsih, DW; Zhou, T; Fukaya, K; Harunari, E; Oku, N; Urabe, D; Igarashi, Y

    JOURNAL OF ANTIBIOTICS   Vol. 75 ( 11 ) page: 610 - 618   2022.11

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1038/s41429-022-00558-y

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  24. Bisprenyl naphthoquinone and chlorinated calcimycin congener bearing thiazole ring from an actinomycete of the genus <i>Phytohabitans</i> Reviewed

    Harunari, E; Mae, S; Fukaya, K; Tashiro, E; Urabe, D; Igarashi, Y

    JOURNAL OF ANTIBIOTICS   Vol. 75 ( 10 ) page: 542 - 551   2022.10

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    DOI: 10.1038/s41429-022-00559-x

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  25. Existence of Syringyl α-Carbonyl-Type Tetrahydrofuran β-β Structure in Hardwood Lignins Reviewed Open Access

    Kishimoto, T; Hiyama, A; Yamashita, A; Takano, T; Tobimatsu, Y; Urabe, D

    ACS SUSTAINABLE CHEMISTRY & ENGINEERING   Vol. 10 ( 37 ) page: 12394 - 12401   2022.9

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    Authorship:Last author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acssuschemeng.2c03861

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  26. Catellatolactams A-C, Plant Growth-Promoting Ansamacrolactams from a Rare Actinomycete of the Genus<i> Catellatospora</i> Reviewed

    Liu, C; Zhang, ZW; Fukaya, K; Urabe, D; Harunari, E; Oku, N; Igarashi, Y

    JOURNAL OF NATURAL PRODUCTS   Vol. 85 ( 8 ) page: 1993 - 1999   2022.8

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    DOI: 10.1021/acs.jnatprod.2c00331

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  27. Stereocontrolled Synthesis of C20S-C26 and C20R-C26 Fragments of Amphidinolide L Reviewed

    Koizumi, J; Tanaka, K; Fukaya, K; Urabe, D

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 87 ( 16 ) page: 11185 - 11195   2022.8

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.joc.2c01497

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  28. Marinoquinolones and Marinobactoic Acid: Antimicrobial and Cytotoxic ortho-Dialkylbenzene-Class Metabolites Produced by a Marine Obligate Gammaproteobacterium of the Genus Marinobacterium Reviewed

    Ul Karim, MR; Fukaya, K; In, Y; Sharma, AR; Harunari, E; Oku, N; Urabe, D; Trianto, A; Igarashi, Y

    JOURNAL OF NATURAL PRODUCTS   Vol. 85 ( 7 ) page: 1763 - 1770   2022.7

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    Language:Japanese   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.jnatprod.2c00281

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  29. RCM approach to the CDE-tricyclic structure of nakiterpiosin Reviewed

    Matsuyuki, Y; Fukaya, K; Urabe, D

    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY   Vol. 86 ( 7 ) page: 832 - 836   2022.6

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1093/bbb/zbac061

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  30. Kumemicinones A-G, Cytotoxic Angucyclinones from a Deep Sea-Derived Actinomycete of the Genus <i>Actinomadura</i> Reviewed

    Zhang, ZW; In, Y; Fukaya, K; Yang, T; Harunari, E; Urabe, D; Imada, C; Oku, N; Igarashi, Y

    JOURNAL OF NATURAL PRODUCTS   Vol. 85 ( 4 ) page: 1098 - 1108   2022.4

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.jnatprod.1c01205

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  31. Effect of pH on the Dehydrogenative Polymerization of Monolignols by Laccases from <i>Trametes versicolor</i> and <i>Rhus vernicifera</i> Reviewed Open Access

    Kishimoto, T; Hiyama, A; Toda, H; Urabe, D

    ACS OMEGA   Vol. 7 ( 11 ) page: 9846 - 9852   2022.3

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    Authorship:Last author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acsomega.2c00144

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  32. Development of a Chiral N-Alkoxyamide Strategy and Application to the Asymmetric Total Synthesis of Fasicularin Reviewed

    Minamikawa, R; Fukaya, K; Kobayashi, A; Komiyaa, Y; Yamamoto, S; Urabe, D; Chida, N; Sato, T

    SYNTHESIS-STUTTGART   Vol. 53 ( 24 ) page: 4621 - 4635   2021.12

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/a-1561-7815

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  33. Nomimicins B-D, new tetronate-class polyketides from a marine-derived actinomycete of the genus <i>Actinomadura</i> Reviewed Open Access

    Zhang, ZW; Zhou, T; Yang, TH; Fukaya, K; Harunari, E; Saito, S; Yamada, K; Imada, C; Urabe, D; Igarashi, Y

    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY   Vol. 17   page: 2194 - 2202   2021.8

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.3762/bjoc.17.141

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  34. TMKS8A, an antibacterial and cytotoxic chlorinated α-lapachone, from a sea slug-derived actinomycete of the genus <i>Streptomyces</i> Reviewed International coauthorship

    Zhang, ZW; Sibero, MT; Kai, AK; Fukaya, K; Urabe, D; Igarashi, Y

    JOURNAL OF ANTIBIOTICS   Vol. 74 ( 7 ) page: 464 - 469   2021.7

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1038/s41429-021-00415-4

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  35. Structure Determination, Biosynthetic Origin, and Total Synthesis of Akazaoxime, an Enteromycin-Class Metabolite from a Marine-Derived Actinomycete of the Genus <i>Micromonospora</i> Reviewed

    Igarashi, Y; Matsuyuki, Y; Yamada, M; Fujihara, N; Harunari, E; Oku, N; Ul Karim, MR; Yang, T; Yamada, K; Imada, C; Fukaya, K; Urabe, D

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 86 ( 9 ) page: 6528 - 6537   2021.5

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.joc.1c00358

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  36. Cyclopeptides from the Mushroom Pathogen Fungus <i>Cladobotryum varium</i> Reviewed

    Zhou, T; Katsuragawa, M; Xing, T; Fukaya, K; Okuda, T; Tokiwa, T; Tashiro, E; Imoto, M; Oku, N; Urabe, D; Igarashi, Y

    JOURNAL OF NATURAL PRODUCTS   Vol. 84 ( 2 ) page: 327 - 338   2021.2

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.jnatprod.0c00980

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  37. SYSTEMATIC SEARCH FOR TRANSITION STATES IN COMPLEX MOLECULES: COMPUTATIONAL ANALYSES OF REGIO- AND STEREOSELECTIVE INTERFLAVAN BOND FORMATION IN FLAVAN-3-OLS Invited Reviewed Open Access

    Urabe, D; Fukaya, K

    HETEROCYCLES   Vol. 102 ( 6 ) page: 1061 - 1082   2021

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    Authorship:Lead author, Corresponding author   Language:Japanese   Publishing type:Research paper (scientific journal)  

    DOI: 10.3987/REV-20-943

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  38. Nocarimidazoles C and D, antimicrobial alkanoylimidazoles from a coral-derived actinomycete <i>Kocuria</i> sp.: application of <SUP>1</SUP><i>J</i><sub><i>C</i>,H</sub> coupling constants for the unequivocal determination of substituted imidazoles and stereochemical diversity of anteisoalkyl chains in microbial metabolites Reviewed International coauthorship Open Access

    Ul Karim, MR; Harunari, E; Sharma, AR; Oku, N; Akasaka, K; Urabe, D; Sibero, MT; Igarashi, Y

    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY   Vol. 16   page: 2719 - 2727   2020.11

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    DOI: 10.3762/bjoc.16.222

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  39. A Computational Study on the Intramolecular C4-C8′ Interflavan Bond Formations of Tethered Catechin Derivatives Reviewed

    Fukaya, K; Saito, A; Nakajima, N; Urabe, D

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   Vol. 93 ( 9 ) page: 1107 - 1113   2020.9

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    Authorship:Last author, Corresponding author   Language:Japanese   Publishing type:Research paper (scientific journal)  

    DOI: 10.1246/bcsj.20200094

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  40. A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus <i>Pseudosporangium</i> Reviewed Open Access

    Saito, S; Atsumi, K; Zhou, T; Fukaya, K; Urabe, D; Oku, N; Ul Karim, MR; Komaki, H; Igarashr, Y

    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY   Vol. 16   page: 1100 - 1110   2020.5

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.3762/bjoc.16.97

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  41. Computational Analysis of the Selective Formation of the C4α-C8′ Bond in the Intermolecular Coupling of Catechin Derivatives Reviewed

    Fukaya, K; Saito, A; Nakajima, N; Urabe, D

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 85 ( 7 ) page: 5010 - 5018   2020.4

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.joc.0c00261

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  42. Microwave-assisted direct transformation of lignocellulose into methyl glycopyranoside in ionic liquid Reviewed

    Kishimoto, T; Saito, M; Suzuki, S; Hamada, M; Nakajima, N; Urabe, D

    HOLZFORSCHUNG   Vol. 74 ( 3 ) page: 313 - 320   2020.3

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    Authorship:Last author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1515/hf-2019-0069

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  43. Biomimetic Oxidation of Monolignol Acetate and <i>p</i>-Coumarate by Silver Oxide in 1,4-Dioxane Reviewed

    Yamashita, A; Kishimoto, T; Hamada, M; Nakajima, N; Urabe, D

    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY   Vol. 68 ( 7 ) page: 2124 - 2131   2020.2

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    Authorship:Last author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.jafc.9b07682

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  44. Computational and Experimental Analysis on the Conformational Preferences of Anticancer Saponin OSW-1 Reviewed

    Fukaya, K; Urabe, D; Hiraizumi, M; Noguchi, K; Matsumoto, T; Sakurai, K

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 85 ( 2 ) page: 339 - 344   2020.1

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    Authorship:Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/acs.joc.9b02085

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  45. Total Synthesis of Talatisamine Reviewed

    Kamakura, D; Todoroki, H; Urabe, D; Hagiwara, K; Inoue, M

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 59 ( 1 ) page: 479 - 486   2020.1

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    DOI: 10.1002/anie.201912737

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  46. A NEW ENTRY TO THE SYNTHESIS OF (±)-β-LYSINE Reviewed Open Access

    Fukaya, K; Kono, Y; Hibi, M; Asano, Y; Urabe, D

    HETEROCYCLES   Vol. 101 ( 2 ) page: 701 - 706   2020.1

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    DOI: 10.3987/COM-19-S(F)38

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  47. Two new aromatic polyketides from a sponge-derived <i>Fusarium</i> Reviewed International coauthorship Open Access

    Sibero, MT; Zhou, T; Fukaya, K; Urabe, D; Radjasa, OKK; Sabdono, A; Trianto, A; Igarashi, Y

    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY   Vol. 15   page: 2941 - 2947   2019.12

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    DOI: 10.3762/bjoc.15.289

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  48. Convergent Total Synthesis of Bioactive Cardenolides Invited Reviewed

    Urabe Daisuke, Inoue Masayuki

    Journal of Synthetic Organic Chemistry, Japan   Vol. 77 ( 5 ) page: 452 - 462   2019.5

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    <p>This account describes convergent total synthesis of bioactive cardenolides, 19-hydroxysarmentogenin-3-<i>O</i>-α-ʟ-rhamnoside, trewianin and ouabagenin. The highly oxygenated structures of the target cardenolides were assembled by applying a convergent and unified strategy. The AB-ring and the D-ring were coupled via formation of the acetal tether and 6-<i>exo</i> radical cyclization. The subsequent aldol reaction enabled the introduction of the three new stereocenters, giving rise to the steroid framework with the <i>cis</i>-fused CD-ring. Attachment of the C17-butenolide by Stille coupling and installation of the ʟ-rhamnose completed the total syntheses of the target cardenolides. The structure-activity relationship study using the synthesized natural and unnatural cardenolides demonstrated the biological importance of the hydroxy groups, the monosaccharide moiety, and the butenolide substructure.</p>

    DOI: 10.5059/yukigoseikyokaishi.77.452

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  49. A Computational Study on the Stereo- and Regioselective Formation of the C4α-C6′ Bond of Tethered Catechin Moieties by an Exhaustive Search of the Transition States Reviewed

    Fukaya, K; Saito, A; Nakajima, N; Urabe, D

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 84 ( 5 ) page: 2840 - 2849   2019.3

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    DOI: 10.1021/acs.joc.8b03263

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  50. SYNTHETIC STUDY OF AN INTERMEDIATE TOWARDS PARACENTRONE Reviewed Open Access

    Kaneyama, T; Fujimaru, K; Takemura, M; Hasegawa, K; Hamada, M; Kishimoto, T; Urabe, D; Nakajima, N

    HETEROCYCLES   Vol. 98 ( 2 ) page: 281 - 294   2019.2

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    DOI: 10.3987/COM-18-S(F)91

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  51. A synergetic effect of ionic liquid and microwave irradiation on the acid-catalyzed direct conversion of cellulose into methyl glucopyranoside Reviewed

    Saito, M; Kishimoto, T; Hamada, M; Nakajima, N; Urabe, D

    HOLZFORSCHUNG   Vol. 72 ( 12 ) page: 1025 - 1030   2018.12

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    DOI: 10.1515/hf-2018-0020

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  52. Total Synthesis and Biological Evaluation of 19-Hydroxysarmentogenin-3-<i>O</i>-α-L-rhamnoside, Trewianin, and Their Aglycons Reviewed

    Urabe, D; Nakagawa, Y; Mukai, K; Fukushima, K; Aoki, N; Itoh, H; Nagatomo, M; Inoue, M

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 83 ( 22 ) page: 13888 - 13910   2018.11

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    DOI: 10.1021/acs.joc.8b02219

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  53. The Computational Examination of the Stereoselective Radical Cyclization of the Complex Molecules Invited Reviewed

    Urabe Daisuke

    Journal of Synthetic Organic Chemistry, Japan   Vol. 76 ( 5 ) page: 430 - 433   2018.5

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    <p>The stereoselectivity of the 7-<i>endo</i> radical cyclization in the syntheses of the complex terpenoids, resiniferatoxin and the model compound of puberulin C, was computationally examined. The DFT calculation of the transition states of the radical cyclizations provided the reasonable explanation for the stereoselective formation of the desired compounds. In the synthesis of the model compound of puberuline C, the energy profile of the radical reaction illustrated the favorable cascade process from the tricyclic intermediate to the pentacyclic compound.</p>

    DOI: 10.5059/yukigoseikyokaishi.76.430

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  54. 12-OH-17,18-Epoxyeicosatetraenoic acid alleviates eosinophilic airway inflammation in murine lungs Reviewed

    Mochimaru, T; Fukunaga, K; Miyata, J; Matsusaka, M; Masaki, K; Kabata, H; Ueda, S; Suzuki, Y; Goto, T; Urabe, D; Inoue, M; Isobe, Y; Arita, M; Betsuyaku, T

    ALLERGY   Vol. 73 ( 2 ) page: 369 - 378   2018.2

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    DOI: 10.1111/all.13297

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  55. A three-component coupling approach to the ACE-ring substructure of C19-diterpene alkaloids Invited Reviewed

    Minagawa, K; Urabe, D; Inoue, M

    JOURNAL OF ANTIBIOTICS   Vol. 71 ( 2 ) page: 326 - 332   2018.2

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    DOI: 10.1038/ja.2017.69

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  56. Synthesis of the Tetracyclic Structure of Batrachotoxin Enabled by Bridgehead Radical Coupling and Pd/Ni-Promoted Ullmann Reaction Reviewed

    Sakata, K; Wang, YH; Urabe, D; Inoue, M

    ORGANIC LETTERS   Vol. 20 ( 1 ) page: 130 - 133   2018.1

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    DOI: 10.1021/acs.orglett.7b03482

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  57. Total Synthesis of Resiniferatoxin Enabled by Radical-Mediated Three-Component Coupling and 7-<i>endo</i> Cyclization Reviewed Open Access

    Hashimoto, S; Katoh, S; Kato, T; Urabe, D; Inoue, M

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 139 ( 45 ) page: 16420 - 16429   2017.11

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    DOI: 10.1021/jacs.7b10177

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  58. Construction of carbocycles initiated by Cu-catalyzed radical reaction of Cl<sub>2</sub>C(CN)<sub>2</sub> Reviewed

    Masuda, K; Tanigawa, M; Nagatomo, M; Urabe, D; Inoue, M

    TETRAHEDRON   Vol. 73 ( 26 ) page: 3596 - 3605   2017.6

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    DOI: 10.1016/j.tet.2017.03.063

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  59. ラジカル反応を基盤とした高酸化度天然物の収束的合成戦略 Invited

    井上 将行, 長友 優典, 占部 大介

    ファルマシア   Vol. 53 ( 9 ) page: 860 - 864   2017

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    炭素骨格が高度に酸素官能基化された天然物(高酸化度天然物)は, しばしば強力な生物活性を示すため, 化学生物学的ツールおよび創薬シード・リード化合物として期待されている. 我々は, 極めて複雑な構造を有し, 重要な生物活性を持つ高酸化度天然物の全合成研究に挑んできた. 本稿では, ラジカル反応を基盤とする官能基許容性が高い収束的合成戦略の開発について述べる. 本戦略によって新しい逆合成解析が可能となり, リアノジンやヒキジマイシン誘導体などの高酸化度分子の効率的合成が実現できた.

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  60. Expanding the scope of Et<sub>3</sub>B/O<sub>2</sub>-mediated coupling reactions of O,Te-acetal Reviewed

    Kamimura, D; Nagatomo, M; Urabe, D; Inoue, M

    TETRAHEDRON   Vol. 72 ( 48 ) page: 7839 - 7848   2016.12

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    DOI: 10.1016/j.tet.2016.04.023

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  61. Construction of the Fused Pentacycle of Talatisamine via a Combination of Radical and Cationic Cyclizations Reviewed

    Tabuchi, T; Urabe, D; Inoue, M

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 81 ( 21 ) page: 10204 - 10213   2016.11

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    DOI: 10.1021/acs.joc.6b01011

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  62. Asymmetric Total Synthesis of Crotophorbolone: Construction of the 5/7/6-Fused Ring System via an α-Alkoxy Bridgehead Radical Reaction Reviewed Open Access

    Urabe, D; Asaba, T; Inoue, M

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   Vol. 89 ( 10 ) page: 1137 - 1144   2016.10

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    DOI: 10.1246/bcsj.20160208

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  63. Symmetry-Driven Strategy for the Assembly of the Core Tetracycle of (+)-Ryanodine: Synthetic Utility of a Cobalt-Catalyzed Olefin Oxidation and α-Alkoxy Bridgehead Radical Reaction Reviewed

    Nagatomo, M; Hagiwara, K; Masuda, K; Koshimizu, M; Kawamata, T; Matsui, Y; Urabe, D; Inoue, M

    CHEMISTRY-A EUROPEAN JOURNAL   Vol. 22 ( 1 ) page: 222 - 229   2016.1

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    DOI: 10.1002/chem.201503640

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  64. Expeditious synthesis of the fused hexacycle of puberuline C via a radical-based cyclization/translocation/cyclization process Reviewed Open Access

    Hagiwara, K; Tabuchi, T; Urabe, D; Inoue, M

    CHEMICAL SCIENCE   Vol. 7 ( 7 ) page: 4372 - 4378   2016

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    DOI: 10.1039/c6sc00671j

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  65. Total Synthesis of Crotophorbolone Reviewed

    Asaba, T; Katoh, Y; Urabe, D; Inoue, M

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 54 ( 48 ) page: 14457 - 14461   2015.11

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    DOI: 10.1002/anie.201509160

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  66. Asymmetric Total Synthesis of (-)-4-Hydroxyzinowol, a Highly Oxygenated Dihydro-β-Agarofuran Reviewed

    Urabe, D; Todoroki, H; Inoue, M

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   Vol. 73 ( 11 ) page: 27 - 37   2015.11

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  67. Total synthesis of four stereoisomers of (5<i>Z</i>,8<i>Z</i>,10<i>E</i>,14<i>Z</i>)-12-hydroxy-17,18-epoxy-5,8,10,14-eicosatetraenoic acid and their <i>anti</i>-inflammatory activities Reviewed

    Goto, T; Urabe, D; Isobe, Y; Arita, M; Inoue, M

    TETRAHEDRON   Vol. 71 ( 43 ) page: 8320 - 8332   2015.10

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    DOI: 10.1016/j.tet.2015.08.047

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  68. Convergent Strategies in Total Syntheses of Complex Terpenoids Reviewed

    Urabe, D; Asaba, T; Inoue, M

    CHEMICAL REVIEWS   Vol. 115 ( 17 ) page: 9207 - 9231   2015.9

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    DOI: 10.1021/cr500716f

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  69. Multifunctionality of the <i>N</i>-Trichloroacetyl Group Developed in the Synthesis of Tetrodotoxin, a Puffer Fish Toxin Reviewed

    Nishikawa, T; Urabe, D; Adachi, M; Isobe, M

    SYNLETT   Vol. 26 ( 14 ) page: 1930 - 1939   2015.9

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    DOI: 10.1055/s-0034-1380781

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  70. Total Synthesis of Four Stereoisomers of (4Z,7Z,10Z,1 2E/1 6Z,1 8<i>E</i>)-1 4,20-hydroxy-4,7,1 0,1 2,1 6,18-docosahexaenoic Acid and Their Anti-inflammatory Activities Reviewed

    Goto, T; Urabe, D; Masuda, K; Isobe, Y; Arita, M; Inoue, M

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 80 ( 15 ) page: 7713 - 7726   2015.8

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    DOI: 10.1021/acs.joc.5b01461

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  71. Radical-Mediated Three-Component Reaction: A Study toward the Total Synthesis of Resiniferatoxin Invited Reviewed Open Access

    Urabe, D

    CHEMICAL & PHARMACEUTICAL BULLETIN   Vol. 63 ( 8 ) page: 565 - 572   2015.8

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    DOI: 10.1248/cpb.c15-00373

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  72. <i>N</i>-(2,3,4,5,6-PENTAFLUOROPHENYL)MALEIMIDE AS A POWERFUL DIENOPHILE IN DEAROMATIZING DIELS-ALDER REACTIONS Invited Reviewed Open Access

    Hagiwara, K; Iwatsu, M; Urabe, D; Inoue, M

    HETEROCYCLES   Vol. 90 ( 1 ) page: 659 - 672   2015.1

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    DOI: 10.3987/COM-14-S(K)23

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  73. A convergent total synthesis of ouabagenin Reviewed Open Access

    Mukai, K; Kasuya, S; Nakagawa, Y; Urabe, D; Inoue, M

    CHEMICAL SCIENCE   Vol. 6 ( 6 ) page: 3383 - 3387   2015

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    DOI: 10.1039/c5sc00212e

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  74. Identification of 14,20-dihydroxy-docosahexaenoic acid as a novel anti-inflammatory metabolite Reviewed Open Access

    Yokokura, Y; Isobe, Y; Matsueda, S; Iwamoto, R; Goto, T; Yoshioka, T; Urabe, D; Inoue, M; Arai, H; Arita, M

    JOURNAL OF BIOCHEMISTRY   Vol. 156 ( 6 ) page: 315 - 321   2014.12

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    DOI: 10.1093/jb/mvu044

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  75. Total Synthesis of (-)-4-Hydroxyzinowol Reviewed

    Todoroki, H; Iwatsu, M; Urabe, D; Inoue, M

    JOURNAL OF ORGANIC CHEMISTRY   Vol. 79 ( 18 ) page: 8835 - 8849   2014.9

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    DOI: 10.1021/jo501666x

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  76. Studies in symmetry-driven synthesis of ryanodol: application of nucleophilic alkynylation for regio- and stereoselective desymmetrization Reviewed

    Hagiwara, K; Urabe, D; Inoue, M

    TETRAHEDRON LETTERS   Vol. 55 ( 28 ) page: 3817 - 3819   2014.7

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    DOI: 10.1016/j.tetlet.2014.05.075

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  77. Total Synthesis of Ryanodol Reviewed

    Nagatomo, M; Koshimizu, M; Masuda, K; Tabuchi, T; Urabe, D; Inoue, M

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 136 ( 16 ) page: 5916 - 5919   2014.4

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    DOI: 10.1021/ja502770n

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  78. Eicosapentaenoic acid is converted <i>via</i> ω-3 epoxygenation to the anti-inflammatory metabolite 12-hydroxy-17,18-epoxyeicosatetraenoic acid Reviewed

    Kubota, T; Arita, M; Isobe, Y; Iwamoto, R; Goto, T; Yoshioka, T; Urabe, D; Inoue, M; Arai, H

    FASEB JOURNAL   Vol. 28 ( 2 ) page: 586 - 593   2014.2

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    DOI: 10.1096/fj.13-236224

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  79. Et B-Mediated Radical-Polar Crossover Reaction for Single-Step Coupling of 0, Te-Acetal, α,β-Unsaturated Ketones, and Aldehydes/Ketones Reviewed

    Kamimura, D; Urabe, D; Nagatomo, M; Inoue, M

    ORGANIC LETTERS   Vol. 15 ( 19 ) page: 5122 - 5125   2013.10

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    DOI: 10.1021/ol402563v

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  80. Concise Synthesis of the Multiply Oxygenated ABC-Ring System of the Dihydro-β-agarofurans Reviewed

    Ishiyama, T; Urabe, D; Fujisawa, H; Inoue, M

    ORGANIC LETTERS   Vol. 15 ( 17 ) page: 4488 - 4491   2013.9

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    DOI: 10.1021/ol402038b

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  81. Preparation and palladium-mediated cross-coupling of α-benzoyloxyalkylzinc bromides Reviewed

    Sakata, K; Urabe, D; Inoue, M

    TETRAHEDRON LETTERS   Vol. 54 ( 32 ) page: 4189 - 4192   2013.8

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    DOI: 10.1016/j.tetlet.2013.05.114

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  82. Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative Reviewed Open Access

    Tabuchi, T; Urabe, D; Inoue, M

    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY   Vol. 9   page: 655 - 663   2013.4

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    DOI: 10.3762/bjoc.9.74

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  83. Stereochemical assignment and anti-inflammatory properties of the omega-3 lipid mediator resolvin E3 Reviewed Open Access

    Isobe, Y; Arita, M; Iwamoto, R; Urabe, D; Todoroki, H; Masuda, K; Inoue, M; Arai, H

    JOURNAL OF BIOCHEMISTRY   Vol. 153 ( 4 ) page: 355 - 360   2013.4

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    DOI: 10.1093/jb/mvs151

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  84. A Convergent Total Synthesis of 19-Hydroxysarmentogenin Reviewed

    Mukai, K; Urabe, D; Kasuya, S; Aoki, N; Inoue, M

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 52 ( 20 ) page: 5300 - 5304   2013

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    DOI: 10.1002/anie.201302067

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  85. A radical-based approach for the construction of the tetracyclic structure of resiniferatoxin Reviewed

    Murai, K; Katoh, S; Urabe, D; Inoue, M

    CHEMICAL SCIENCE   Vol. 4 ( 6 ) page: 2364 - 2368   2013

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    DOI: 10.1039/c3sc50329a

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  86. Symmetry-driven synthesis of 9-demethyl-10,15-dideoxyryanodol Reviewed

    Urabe, D; Nagatomo, M; Hagiwara, K; Masuda, K; Inoue, M

    CHEMICAL SCIENCE   Vol. 4 ( 4 ) page: 1615 - 1619   2013

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    DOI: 10.1039/c3sc00023k

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  87. Symmetry-driven total synthesis of merrilactone A and resolvin E2 Reviewed

    Masayuki Inoue, Daisuke Urabe

    Strategies and Tactics in Organic Synthesis   Vol. 9   page: 149 - 175   2013

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    DOI: 10.1016/B978-0-08-099362-1.00005-9

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  88. SELECTIVE INTRODUCTION OF FOUR CONTIGUOUS STEREOCENTERS ON THE B-RING OF 4-HYDROXYZINOWOL Invited Reviewed Open Access

    Iwatsu, M; Urabe, D; Todoroki, H; Masuda, K; Inoue, M

    HETEROCYCLES   Vol. 86 ( 1 ) page: 181 - 188   2012.12

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    DOI: 10.3987/COM-12-S(N)76

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  89. Intermolecular Radical Reaction of <i>O</i>,<i>Se</i>-Acetals Generated via Seleno-Pummerer Rearrangement Reviewed

    Urabe, D; Yamaguchi, H; Someya, A; Inoue, M

    ORGANIC LETTERS   Vol. 14 ( 15 ) page: 3842 - 3845   2012.8

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    DOI: 10.1021/ol301482f

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  90. Total syntheses of four possible stereoisomers of resolvin E3 Reviewed

    Urabe, D; Todoroki, H; Masuda, K; Inoue, M

    TETRAHEDRON   Vol. 68 ( 15 ) page: 3210 - 3219   2012.4

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    DOI: 10.1016/j.tet.2012.02.045

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  91. Identification and Structure Determination of Novel Anti-inflammatory Mediator Resolvin E3, 17,18-Dihydroxyeicosapentaenoic Acid Reviewed Open Access

    Isobe, Y; Arita, M; Matsueda, S; Iwamoto, R; Fujihara, T; Nakanishi, H; Taguchi, R; Masuda, K; Sasaki, K; Urabe, D; Inoue, M; Arai, H

    JOURNAL OF BIOLOGICAL CHEMISTRY   Vol. 287 ( 13 ) page: 10525 - 10534   2012.3

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    DOI: 10.1074/jbc.M112.340612

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  92. Application of α-Alkoxy Bridgehead Radical for Coupling of Oxygenated Carbocycles Reviewed

    Urabe, D; Yamaguchi, H; Inoue, M

    ORGANIC LETTERS   Vol. 13 ( 18 ) page: 4778 - 4781   2011.9

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    DOI: 10.1021/ol201758a

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  93. Total Synthesis and Bioactivities of Two Proposed Structures of Maresin Reviewed

    Sasaki, K; Urabe, D; Arai, H; Arita, M; Inoue, M

    CHEMISTRY-AN ASIAN JOURNAL   Vol. 6 ( 2 ) page: 534 - 543   2011.2

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    DOI: 10.1002/asia.201000494

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  94. ASYMMETRIC SYNTHESES OF HIGHLY FUNCTIONALIZED BICYCLO[2.2.2]OCTENE DERIVATIVES Invited Reviewed Open Access

    Iwatsu, M; Urabe, D; Inoue, M

    HETEROCYCLES   Vol. 82 ( 1 ) page: 491 - 504   2010.12

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    DOI: 10.3987/COM-10-S(E)22

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  95. New Syntheses of E7389 C14-C35 and Halichondrin C14-C38 Building Blocks: Reductive Cyclization and Oxy-Michael Cyclization Approaches Reviewed

    Dong, CG; Henderson, JA; Kaburagi, Y; Sasaki, T; Kim, DS; Kim, JT; Urabe, D; Guo, HB; Kishi, Y

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 131 ( 43 ) page: 15642 - 15646   2009.11

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    DOI: 10.1021/ja9058487

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  96. Toolbox Approach to the Search for Effective Ligands for Catalytic Asymmetric Cr-Mediated Coupling Reactions Reviewed

    Guo, HB; Dong, CG; Kim, DS; Urabe, D; Wang, JS; Kim, JT; Liu, X; Sasaki, T; Kishi, Y

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   Vol. 131 ( 42 ) page: 15387 - 15393   2009.10

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    DOI: 10.1021/ja905843e

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    PubMed

  97. Total Synthesis and Bioactivity of Resolvin E2 Reviewed

    Ogawa, S; Urabe, D; Yokokura, Y; Arai, H; Arita, M; Inoue, M

    ORGANIC LETTERS   Vol. 11 ( 16 ) page: 3602 - 3605   2009.8

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ol901350g

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    PubMed

  98. Total syntheses of sesquiterpenes from <i>Illicium</i> species Invited Reviewed

    Urabe, D; Inoue, M

    TETRAHEDRON   Vol. 65 ( 32 ) page: 6271 - 6289   2009.8

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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tet.2009.06.010

    Web of Science

  99. SYNTHESES OF <i>N</i>-ACYLISOXAZOLIDINE DERIVATIVES, RELATED TO A PARTIAL STRUCTURE FOUND IN ZETEKITOXIN AB, A GOLDEN FROG POISON Reviewed Open Access

    Nishikawa, T; Urabe, D; Isobe, M

    HETEROCYCLES   Vol. 79   page: 379 - 385   2009.4

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.3987/COM-08-S(D)44

    Open Access

    Web of Science

  100. One-pot transformation of trichloroacetamide into readily deprotectable carbamates Reviewed

    Nishikawa, T; Urabe, D; Tomita, M; Tsujimoto, T; Iwabuchi, T; Isobe, M

    ORGANIC LETTERS   Vol. 8 ( 15 ) page: 3263 - 3265   2006.7

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    DOI: 10.1021/ol061123c

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  101. An efficient total synthesis of optically active tetrodotoxin from levoglucosenone Reviewed

    Urabe, D; Nishikawa, T; Isobe, M

    CHEMISTRY-AN ASIAN JOURNAL   Vol. 1 ( 1-2 ) page: 125 - 135   2006.7

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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/asia.200600038

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    PubMed

  102. Synthesis of functionalized cyclopentane for pactamycin, a potent antitumor antibiotic Reviewed

    Tsujimoto, T; Nishikawa, T; Urabe, D; Isobe, M

    SYNLETT   ( 3 ) page: 433 - 436   2005.2

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1055/s-2004-837223

    Web of Science

  103. A novel deprotection of trichloroacetamide Reviewed

    Urabe, D; Sugino, K; Nishikawa, T; Isobe, M

    TETRAHEDRON LETTERS   Vol. 45 ( 51 ) page: 9405 - 9407   2004.12

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    Authorship:Lead author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1016/j.tetlet.2004.10.099

    Web of Science

  104. Stereocontrolled synthesis of 8,11-dideoxytetrodotoxin, an unnatural analogue of puffer fish toxin Reviewed Open Access

    Nishikawa, T; Urabe, D; Yoshida, K; Iwabuchi, T; Asai, M; Isobe, M

    CHEMISTRY-A EUROPEAN JOURNAL   Vol. 10 ( 2 ) page: 452 - 462   2004.1

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/chem.200305111

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  105. An efficient total synthesis of optically active tetrodotoxin Reviewed

    Nishikawa, T; Urabe, D; Isobe, M

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Vol. 43 ( 36 ) page: 4782 - 4785   2004

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/anie.200460293

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  106. Total syntheses of 11-deoxytetrodotoxin and 8,11-dideoxytetrodotoxin Reviewed Open Access

    Nishikawa, T; Urabe, D; Yoshida, K; Iwabuchi, T; Asai, M; Isobe, M

    PURE AND APPLIED CHEMISTRY   Vol. 75 ( 2-3 ) page: 251 - 257   2003.2

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1351/pac200375020251

    Web of Science

  107. Stereocontrolled synthesis of 8,11-dideoxytetrodotoxin, unnatural analogue of puffer fish toxin Reviewed

    Nishikawa, T; Urabe, D; Yoshida, K; Iwabuchi, T; Asai, M; Isobe, M

    ORGANIC LETTERS   Vol. 4 ( 16 ) page: 2679 - 2682   2002.8

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    Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1021/ol026177a

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▼display all

Books 1

  1. トップドラッグから学ぶ創薬化学 第II部 12.オレフィンメタセシス

    占部 大介

    東京化学同人  2012 

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    Total pages:199   Language:Japanese Book type:Textbook, survey, introduction

    CiNii Research

MISC 148

  1. Macrolactam-type secondary metabolite produced by actinomycete stabilizes cell membranes and promotes thermotolerance

    齋藤駿, 奥村薫里香, 深谷圭介, 占部大介, 荒井緑

    日本農芸化学会大会講演要旨集(Web)   Vol. 2025   2025

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    Language:Japanese   Publishing type:Research paper, summary (national, other academic conference)  

    J-GLOBAL

    researchmap

  2. Isolation, structure determination, and analysis for thermotolerance-promoting mechanism of heat shock metabolite (HSM) produced by Streptomyces sp. JA74

    奥村薫里香, 齋藤駿, 船山佳世, 深谷圭介, 占部大介, 荒井緑

    日本放線菌学会大会講演要旨集   Vol. 37th   2023

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    Language:Japanese   Publishing type:Research paper, summary (national, other academic conference)  

    J-GLOBAL

    researchmap

  3. Chemical structure of oligolignols by dehydrogenative polymerization of sinapyl alcohol

    山口愛由, 岸本崇生, 占部大介

    日本木材学会大会研究発表要旨集(完全版)(CD-ROM)   Vol. 72nd   2022

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    Authorship:Last author   Language:Japanese   Publishing type:Research paper, summary (national, other academic conference)  

    J-GLOBAL

    researchmap

  4. Reaction mechanism of the conversion of cellulose into methyl glucoside

    藤森愛仁, 岸本崇生, 小杉瑞穂, 占部大介

    日本木材学会大会研究発表要旨集(完全版)(CD-ROM)   Vol. 72nd   2022

  5. Total synthesis and SAR study of akazaoxime

    松雪洋恵, 藤原和, 深谷圭介, 深谷圭介, KARIM Md. Pokon Ul, 五十嵐康弘, 五十嵐康弘, 占部大介, 占部大介

    日本薬学会年会要旨集(Web)   Vol. 141st   2021

  6. 異物抱合酵素発現酵母を用いたピセアタンノール抱合代謝物調製技術の開発

    中山舞, 西川美宇, 安田佳織, 深谷圭介, 占部大介, 榊利之, 生城真一

    ビタミン   Vol. 95 ( 4 )   2021

  7. Comprehensive synthesis of conjugated metabolites of stilbenoid using xenobiotic metabolizing enzymes expressing yeast

    中山舞, 西川美宇, 深谷圭介, 占部大介, 榊利之, 生城真一

    日本農芸化学会大会講演要旨集(Web)   Vol. 2021   2021

  8. Synthetic study of deoxynybomycin by using the desymmetrizing amidation

    甲斐瑛歩, 深谷圭介, 深谷圭介, 濱田昌弘, 濱田昌弘, 馬場理, 占部大介, 占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2021   2021

  9. Conversion of glucomannan and xylan into octyl glycoside by microwave heating in ionic liquid

    岸本崇生, 渡部芙有子, 占部大介

    セルロース学会年次大会講演要旨集   Vol. 28th   2021

  10. Synthetic study of amphidinolide L

    小泉潤, 田中芳, 深谷圭介, 深谷圭介, 占部大介, 占部大介

    日本薬学会年会要旨集(Web)   Vol. 141st   2021

  11. Synthetic Study of Alchivemycin A

    印藤寛二, 占部大介, 占部大介, 深谷圭介, 深谷圭介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2021   2021

  12. Synthetic Study of 17-Hydroxydocosahexaenoic acid

    岩井柚樹, 深谷圭介, 深谷圭介, 占部大介, 占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2021   2021

  13. Formation of α-carbonyl type β-β structures by enzymatic plymerization of sinapyl alcohol

    岸本崇生, 桧山歩, 山下綾菜, 占部大介

    日本木材学会大会研究発表要旨集(完全版)(CD-ROM)   Vol. 71st   2021

  14. Synthetic Study of Formosalide A

    茂住梨紗, 駒津友美, 深谷圭介, 深谷圭介, 占部大介, 占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2021   2021

  15. Synthetic study of veratridine

    塩野啓太, 深谷圭介, 深谷圭介, 占部大介, 占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2021   2021

  16. Synthetic study of side chains of Nakiterpiosin

    堀江智也, 深谷圭介, 深谷圭介, 占部大介, 占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2021   2021

  17. 抱合酵素発現酵母菌体を用いた食品中機能性成分抱合代謝物の網羅的合成

    中山舞, 西川美宇, 深谷圭介, 占部大介, 榊利之, 生城真一

    日本農芸化学会西日本支部大会およびシンポジウム講演要旨集   Vol. 2020 (CD-ROM)   2020

  18. Preparation and characterization of conjugated metabolites of piceatannol using xenobiotic metabolizing enzymes expressing yeast

    中山舞, 西川美宇, 安田佳織, 深谷圭介, 占部大介, 榊利之, 生城真一

    日本農芸化学会大会講演要旨集(Web)   Vol. 2020   2020

  19. 有機合成化学と計算化学を基盤とした17-ヒドロペルオキシドコサヘキサエン酸の生物有機化学的研究

    占部大介

    医科学応用研究財団研究報告(CD-ROM)   Vol. 37   2020

  20. Synthetic study of Alchivemycin A

    印藤寛二, 深谷圭介, 深谷圭介, 占部大介, 占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2020   2020

  21. ウルシおよびカワラタケラッカーゼによるモノリグノールの脱水素重合

    檜山歩, 岸本崇生, 占部大介

    日本木材学会大会研究発表要旨集(完全版)(CD-ROM)   Vol. 70th   2020

  22. Synthetic study of Amphidinolide L

    小泉潤, 深谷圭介, 深谷圭介, 占部大介, 占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2020   2020

  23. Synthetic study of Nakiterpiosin

    松雪洋恵, 深谷圭介, 深谷圭介, 占部大介, 占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2020   2020

  24. Synthetic study of Formosalide A

    茂住梨紗, 深谷圭介, 深谷圭介, 占部大介, 占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2020   2020

  25. 有機溶媒中でのコニフェリルアルコールの脱水素重合

    山下綾菜, 岸本崇生, 濱田昌弘, 中島範行, 占部大介

    日本木材学会大会研究発表要旨集(完全版)(CD-ROM)   Vol. 69th   2019

  26. 異物抱合酵素発現酵母菌体を用いたスチルベン化合物の抱合代謝物の酵素合成

    中山舞, 西川美宇, 西川美宇, 安田佳織, 鎌倉昌樹, 深谷圭介, 占部大介, 榊利之, 生城真一

    日本農芸化学会大会講演要旨集(Web)   Vol. 2019   2019

  27. 異物抱合酵素発現酵母を用いたスチルベン化合物の抱合反応解析及び抱合体調製

    中山舞, 西川美宇, 安田佳織, 深谷圭介, 占部大介, 榊利之, 生城真一

    ビタミン   Vol. 93 ( 4 )   2019

  28. 未研究希少放線菌Pseudosporangium属が生産する二次代謝物の精密解析

    齋藤駿, 渥美幸大, 深谷圭介, 占部大介, 小牧久幸, 五十嵐康弘

    日本放線菌学会大会講演要旨集   Vol. 34th   2019

  29. 計算化学を活用した天然物合成へのアプローチ

    占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2019   2019

  30. カテキン誘導体の分子内カップリングに対する計算化学的手法による研究

    深谷圭介, 深谷圭介, 齊藤安貴子, 中島範行, 中島範行, 占部大介, 占部大介

    日本化学会春季年会講演予稿集(CD-ROM)   Vol. 99th   2019

  31. カテキン誘導体の分子内カップリングにおける計算化学的研究

    深谷圭介, 深谷圭介, 齊藤安貴子, 中島範行, 中島範行, 占部大介, 占部大介

    次世代を担う有機化学シンポジウム講演要旨集   Vol. 17th   2019

  32. イオン液体中でのマイクロ波加熱によるセルロースのオクチルグルコシドへの直接変換

    岸本崇生, 樋口未来, 占部大介

    セルロース学会年次大会講演要旨集   Vol. 26th   2019

  33. アンフィジノリドLの合成研究

    小泉潤, 深谷圭介, 占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2019   2019

  34. 17-ヒドロぺルオキシドコサヘキサエン酸の合成研究

    岩井柚樹, 深谷圭介, 占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2019   2019

  35. A study toward the design and synthesis of an anti-tumor lipid mediator by controlling the conformation

    占部大介

    東京生化学研究会助成研究報告集   Vol. 33   2019

  36. ナキテルピオシン側鎖部の合成研究

    堀江智也, 深谷圭介, 深谷圭介, 占部大介, 占部大介

    日本農芸化学会関西支部講演会講演要旨集   Vol. 510th   2019

  37. モノリグノールの脱水素重合に及ぼす有機溶媒の効果

    山下綾菜, 岸本崇生, 濱田昌弘, 中島範行, 占部大介

    日本木材学会中部支部大会講演要旨集   ( 29 )   2019

  38. 全合成の現在と未来:戦略面から見た全合成と人工分子創製の重要性

    井上将行, 占部大介

    CSJ Current Review   ( 27 )   2018

  39. The Computational Examination of the Stereoselective Radical Cyclization of the Complex Molecules Reviewed

    占部大介

    有機合成化学協会誌   Vol. 76 ( 5 ) page: 430 - 433   2018

  40. 天然物全合成の基礎 直線的合成と収束的合成の基礎

    占部大介

    CSJ Current Review   ( 27 )   2018

  41. 計算化学的手法によるホルモサリドAの構造推定

    占部大介

    日本農芸化学会大会講演要旨集(Web)   Vol. 2018   2018

  42. オイオニミノールの全合成研究

    王瀛華, 藤澤博基, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 138th   2018

  43. イオン液体中でのマイクロ波加熱によるリグノセルロースのメチルグリコシドへの変換

    斉藤真冬, 岸本崇生, 濱田昌弘, 中島範行, 占部大介

    日本木材学会大会研究発表要旨集(完全版)(CD-ROM)   Vol. 68th   2018

  44. イオン液体に溶解した木質バイオマスのマイクロ波加熱によるメチルグルコシドへの変換

    斉藤真冬, 岸本崇生, 濱田昌弘, 中島範行, 占部大介

    セルロース学会年次大会講演要旨集   Vol. 25th   2018

  45. PEG-HRPを用いた有機溶媒中でのコニフェリルアルコールの脱水素重合

    山下綾菜, 岸本崇生, 濱田昌弘, 中島範行, 占部大介

    リグニン討論会講演集   Vol. 63rd   2018

  46. 高酸化度アガロフランセスキテルペンの全合成研究

    藤澤博基, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 138th   2018

  47. 酸化銀を用いたアシル化モノリグノールの酸化カップリング

    山下綾菜, 岸本崇生, 濱田昌弘, 中島範行, 占部大介

    日本木材学会大会研究発表要旨集(完全版)(CD-ROM)   Vol. 68th   2018

  48. コニフェリルアルコールの脱水素重合に及ぼす有機溶媒の効果

    山下綾菜, 岸本崇生, 濱田昌弘, 中島範行, 占部大介

    日本木材学会中部支部大会講演要旨集   ( 28 )   2018

  49. レジニフェラトキシンC環の効率的合成

    加藤雄大, 橋本哲, 加藤駿一郎, 占部大介, 井上将行

    日本薬学会関東支部大会講演要旨集   Vol. 61st   2017

  50. レジニフェラトキシンの全合成研究

    加藤駿一郎, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 137th   2017

  51. Total Synthesis of Resiniferatoxin

    橋本哲, 加藤駿一郎, 加藤雄大, 占部大介, 井上将行

    天然有機化合物討論会講演要旨集(Web)   Vol. 59th   2017

  52. 連続ラジカル反応を鍵としたトウセンダニンの合成研究

    武藤大之, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 137th   2017

  53. カルデノリド類の全合成

    中川雄喜, 向井健, 福島圭一郎, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 137th   2017

  54. オイオニミノールの全合成研究

    王瀛華, 藤澤博基, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 137th   2017

  55. イオン液体中でのマイクロ波照射によるスギ木粉からのメチルグリコシドの合成

    斉藤真冬, 岸本崇生, 濱田昌弘, 中島範行, 占部大介

    リグニン討論会講演集   Vol. 62nd   2017

  56. イオン液体中でのマイクロ波加熱によるセルロースのメチルグルコシドへの直接変換

    斉藤真冬, 岸本崇生, 濱田昌弘, 中島範行, 占部大介

    セルロース学会年次大会講演要旨集   Vol. 24th   2017

  57. イオン液体中でのマイクロ波加熱によるスギ(Cryptomeria japonica)木粉からのメチルグリコシドの合成

    斉藤真冬, 岸本崇生, 濱田昌弘, 中島範行, 占部大介

    日本木材学会中部支部大会講演要旨集   ( 27 )   2017

  58. 酸化銀によるシナピルp-クマレートの酸化カップリング

    山下綾菜, 岸本崇生, 濱田昌弘, 中島範行, 占部大介

    リグニン討論会講演集   Vol. 62nd   2017

  59. タラチサミンAE環の効率的合成

    島川典, 鎌倉大貴, 占部大介, 萩原浩一, 井上将行

    日本薬学会関東支部大会講演要旨集   Vol. 61st   2017

  60. チグリアン・ダフナンジテルペン類の合成研究

    廣瀬哲, 浅羽太郎, 占部大介, 井上将行

    有機合成シンポジウム講演要旨集   Vol. 112th   2017

  61. 高酸化度アガロフラン型セスキテルペンの全合成研究

    藤澤博基, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 136th   2016

  62. オイオニミノールの全合成研究

    王瀛華, 藤澤博基, 占部大介, 井上将行

    日本薬学会関東支部大会講演要旨集   Vol. 60th (CD-ROM)   2016

  63. タラチサミンの全合成研究

    鎌倉大貴, 轟木秀憲, 占部大介, 井上将行

    反応と合成の進歩シンポジウム講演要旨集   Vol. 42nd   2016

  64. ラジカル反応を基盤としたチグリアン・ダフナンジテルペン類の合成戦略

    占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 136th   2016

  65. ラジカル-極性交差型反応を鍵としたC19ジテルペンアルカロイドの合成研究

    皆川功亮, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 136th   2016

  66. ブリオフィリンCの全合成研究

    中川雄喜, 向井健, 占部大介, 井上将行

    有機合成シンポジウム講演要旨集   Vol. 109th   2016

  67. バトラコトキシンの全合成研究

    坂田光命, 占部大介, 井上将行

    有機合成シンポジウム講演要旨集   Vol. 110th   2016

  68. チグリアン・ダフナンジテルペン類の網羅的全合成研究

    浅羽太郎, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 136th   2016

  69. タンデムラジカル環化を用いたプベルリンCの合成研究

    占部大介, 萩原浩一, 井上将行

    日本薬学会関東支部大会講演要旨集   Vol. 60th (CD-ROM)   2016

  70. タラチサミンの合成研究

    鎌倉大貴, 轟木秀憲, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 136th   2016

  71. レジニフェラトキシンの全合成研究

    橋本哲, 加藤駿一郎, 村井耕一, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 135th   2015

  72. 合成化学者の特権!? 新規抗炎症性脂質メディエーターの発見 Reviewed

    占部 大介

    ファルマシア   Vol. 51 ( 8 ) page: 800 - 800   2015

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    化学者は天然物やその類縁体の多段階合成において,多くの新規化合物に遭遇する.それらの中には標的化合物よりも重要な化合物が紛れ込むことがある.本稿では,エポキシイソプロスタンEC(<b>1</b>)の合成において予期せぬ<b>2</b>が得られたことに端を発し,種々の類縁体を合成することで<b>1</b>の活性発現において重要な構造変換を推定した論文を紹介する.<br>なお,本稿は下記の文献に基づいて,その研究成果を紹介するものである.<br>1) Egger J. <i>et al</i>., <i>J. Am. Chem. Soc</i>., 136, 17382-17385 (2014).<br>2) Egger J. <i>et al</i>., <i>Angew. Chem. Int. Ed</i>., 52, 5382-5385 (2013).<br>3) Jung M. E. <i>et al</i>., <i>Org. Lett</i>., 10, 4207-4209 (2008).

    DOI: 10.14894/faruawpsj.51.8_800

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  73. レジニフェラトキシンの全合成研究

    橋本哲, 加藤駿一郎, 村井耕一, 占部大介, 井上将行

    反応と合成の進歩シンポジウム講演要旨集   Vol. 41st   2015

  74. 高酸化度アガロフランセスキテルペンの全合成研究

    藤澤博基, 石山備凡, 占部大介, 井上将行

    有機合成化学セミナー講演予稿集   Vol. 32nd   2015

  75. 高酸化度アガロフランセスキテルペンの全合成研究

    藤澤博基, 石山備凡, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 135th   2015

  76. タラチサミンの全合成研究

    轟木秀憲, 鎌倉大貴, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 135th   2015

  77. ラジカル反応を基盤とした複雑天然物の全合成研究

    占部大介

    日本薬学会年会要旨集(CD-ROM)   Vol. 135th   2015

  78. プベルリンCの合成研究

    萩原浩一, 田渕俊樹, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 135th   2015

  79. プベルリンCの全合成研究

    萩原浩一, 田渕俊樹, 占部大介, 井上将行

    次世代を担う有機化学シンポジウム講演要旨集   Vol. 13th   2015

  80. レジニフェラトキシンの全合成研究

    加藤駿一郎, 村井耕一, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 134th   2014

  81. 結晶スポンジ法の多段階合成における簡便な構造解析手法としての応用

    佐藤寛, 荒井達彦, 吉岡翔太, 猪熊泰英, 占部大介, 井上将行, 藤田誠, 藤田誠

    日本化学会講演予稿集   Vol. 94th ( 4 )   2014

  82. 高酸化度アガロフラン型セスキテルペンの全合成研究

    藤澤博基, 石山備凡, 占部大介, 井上将行

    有機合成シンポジウム講演要旨集   Vol. 106th   2014

  83. クロトホルボロンの全合成研究

    浅羽太郎, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 134th   2014

  84. クロトホルボロンの全合成

    浅羽太郎, 嘉藤裕樹, 占部大介, 井上将行

    反応と合成の進歩シンポジウム講演要旨集   Vol. 40th   2014

  85. ウアバゲニンの全合成

    占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 134th   2014

  86. (±)-リアノドールの全合成

    小清水正樹, 長友優典, 枡田健吾, 田渕俊樹, 占部大介, 井上将行

    次世代を担う有機化学シンポジウム講演要旨集   Vol. 12th   2014

  87. Asymmetric Total Synthesis of (+)-Ryanodine

    Masuda Kengo, Nagatomo Masanori, Koshimizu Masaki, Hagiwara Koji, Tabuchi Toshiki, Urabe Daisuke, Inoue Masayuki

    Symposium on the Chemistry of Natural Products, symposium papers   Vol. 56th ( 0 ) page: Oral25   2014

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    <p>(+)-Ryanodine (1) has potent modulatory activity toward an intracellular calcium release channel known as the ryanodine receptor. Compound 1 possesses five hydroxy groups, a hemiacetal, a pyrrole-carboxylate ester, and eleven consecutive stereocenters including eight tetrasubstituted carbons within the complex pentacyclic ABCDE-ring system. The densely functionalized structure of 1 poses a formidable synthetic challenge. Herein, we report the first asymmetric total synthesis of 1.</p><p>To take advantage of the intrinsic symmetric substructure of 1, we designed C<sub>2</sub>-symmetric tricycle 5 as the key intermediate. First, dearomatizing Diels-Alder reaction of 3 and 4, followed by asymmetric methanolysis, led to optically active bicyclo[2.2.2]octene (+)-12. The pairwise functionalizations of C<sub>2</sub>-symmetric compounds and construction of the AB-ring system via the transannular aldol reaction afforded the key intermediate 5.</p><p>The carbon skeleton of 1 was constructed from 5. After Co (II)-catalyzed oxidative desymmetrization of C<sub>2</sub>-symmetric tricycle 5, the bridgehead radical allylation of 22 installed the C11-tetrasubstituted stereocenter of 6. The regio- and stereoselective introduction of the two carbon chains at the C6 and C2-position and construction of the C-ring by ring-closing metathesis completed the synthesis of 8, which has the entire carbon skeleton of 1.</p><p>The asymmetric total synthesis of (+)-ryanodine (1) has been accomplished from 8. Removal of C6-TMS group and the acetonide, followed by the stereoselective reduction of C3-ketone, afforded pentaol 31. The regioselective protection of the four tertiary hydroxy groups of 31yielded bisboronate 32. Condensation of 32 with protected glycine Dgave rise to glycine ester 33. Treatment of 33 with vinamidinium salt E efficiently constructed the pyrrole-carboxylate ester at the C3-position, generating 35. Finally, deprotection and hydrogenation of the isopropenyl group delivered (+)-ryanodine (1).</p>

    DOI: 10.24496/tennenyuki.56.0_Oral25

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  88. バトラコトキシンの合成研究

    坂田光命, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 134th   2014

  89. リアノドールの全合成

    小清水正樹, 長友優典, 枡田健吾, 萩原幸司, 田渕俊樹, 占部大介, 井上将行

    有機合成化学セミナー講演予稿集   Vol. 31st   2014

  90. プベルリンCの合成研究

    萩原浩一, 田渕俊樹, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 134th   2014

  91. プベルリンCの合成研究

    萩原浩一, 田渕俊樹, 占部大介, 井上将行

    有機合成シンポジウム講演要旨集   Vol. 105th   2014

  92. レジニフェラトキシンの合成研究

    加藤駿一郎, 村井耕一, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 133rd   2013

  93. Synthetic study of 4-hydroxyzinowol

    Todoroki Hidenori, Iwatsu Masahumi, Masuda Kengo, Urabe Daisuke, Inoue Masayuki

    Symposium on the Chemistry of Natural Products, symposium papers   Vol. 55th ( 0 ) page: Oral23   2013

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    <p>4-Hydroxyzinowol (1), a member of dihydo-β-agarofuran sesequiterpenoids, has potent inhibitory activity against P-glycoprotein, which excretes various small molecules across the cell membrane. More than 400 dihydo-β-agarofuran derivatives have been isolated to date, and many of them exhibit various biological activities such as antitumor, anti-inflammatory, immunosuppressive and anti-HIV activities. From the synthetic point of view, the highly oxygenated tricyclic structure of 1 (ABC-ring) decorated with three contiguous tetrasubstituted carbons (C4, 5, and 10) poses a formidable challenge. To establish a general synthetic route to dihydro-β-agarofurans, we selected 4-hydroxyzinowol as the initial synthetic target. Herein we report the stereoselective synthesis of the core structure of 1.</p><p>The synthesis started from 1,5-dihydroxynaphthalene (3). Dearomatization of the B-ring followed by Rhodium-catalyzed asymmetric 1,4-addition of isopropenyl group to enone 11 introduced the three-carbon unit. Hypervalent-iodine promoted C8-hydroxylation of ketone 13 gave 16 stereoselectively. Then, the following 7-step sequence, including stereoselective reduction of C6 and C9 ketones, led to 24, which has four contiguous stereocenters (C6, 7, 8, and 9) of 1.</p><p>The core structure of 1, bearing the three consecutive tetrasubstituted carbons (C4, 5, and 10) was constructed through the following transformations. The dearomatization of 24 with NaIO<sub>4 </sub>generated the C5-tetrasubstituted carbon via oxidation of the A-ring and simultaneous epoxide formation with the C6 hydroxyl group. The stereo- and regioselective Diels-Alder reaction of diene 26with ethynyl p-tolylsulfone installed the C10-quaternary carbon center to produce 30. Then, the etherification and introduction of the methyl group at C4-ketone realized formation of the C-ring and the three consecutive tetrasubstituted carbons of 1. Finally, the 8-step transformation delivered 41 bearing the entire structure of 1. </p>

    DOI: 10.24496/tennenyuki.55.0_Oral23

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  94. エイコサペンタエン酸由来の抗炎症性代謝物Resolvin E3の新規同定

    磯部洋輔, 有田誠, 有田誠, 中西広樹, 田口良, 占部大介, 井上将行, 新井洋由

    ビタミン   Vol. 87 ( 4 ) page: 223 - 223   2013

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    DOI: 10.20632/vso.87.4_223_1

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  95. α-アシルオキシ有機亜鉛化合物によるクロスカップリング反応の開発

    坂田光命, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 133rd   2013

  96. クロトホルボロンの合成研究

    浅羽太郎, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 133rd   2013

  97. レイサンチンBの合成研究

    轟木秀憲, 枡田健吾, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 133rd   2013

  98. トウセンダニンの合成研究

    福島圭一郎, 青木直人, 占部大介, 井上将行

    日本薬学会年会要旨集(CD-ROM)   Vol. 133rd   2013

  99. タラチサミンの全合成研究

    田渕俊樹, 占部大介, 井上将行

    反応と合成の進歩シンポジウム講演要旨集   Vol. 39th   2013

  100. セラングリンの合成研究

    藤澤博基, 石丸備凡, 占部大介, 井上将行

    日本薬学会関東支部大会講演要旨集   Vol. 57th   2013

  101. レジニフェラトキシンの全合成研究

    村井耕一, 加藤駿一郎, 占部大介, 井上将行

    次世代を担う有機化学シンポジウム講演要旨集   Vol. 10th   2012

  102. 抗炎症活性をもつ新規脂質メディエーターの合成

    後藤智見, 占部大介, 増田功嗣, 井上将行

    メディシナルケミストリーシンポジウム講演要旨集   Vol. 30th   2012

  103. レジニフェラトキシンの合成研究

    加藤駿一郎, 村井耕一, 占部大介, 井上将行

    日本薬学会関東支部大会講演要旨集   Vol. 56th   2012

  104. 43 Total Synthesis of 19-Hydroxy-Sarmentogenin(Oral Presentation)

    Mukai Ken, Kasuya Satoshi, Aoki Naoto, Urabe Daisuke, Inoue Masayuki

    Symposium on the Chemistry of Natural Products, symposium papers   Vol. 54th ( 0 ) page: 253 - 258   2012

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    19-Hydroxy-sarmentogenin (3) is an aglycon of 19-hydroxy-sarmentogenin-3β-O-β-6-deoxyguloside (2), a cytotoxic cardenolide carbohydrate. The cardenolide family is structurally characterized by the oxygenated steroidal skeleton, which is composed of cis-fused AB- and CD-ring and β-oriented C17-butenolide. To establish a unified synthetic route to the oxygenated cardenolides, we selected 3 as the initial synthetic target. Here we report a total synthesis of 3. For efficient construction of the oxygenated steroidal structure of 3, the new convergent strategy was designed. Specifically, the functionalized AB-ring 4 and the D-ring 5 were coupled via the acetal coupling under the mild conditions, affording bromoacetal 6. The C9-11 bond of 20 was stereoselectively formed through 6-membered ring cyclization of the C11-carbon radical that was generated by treating 6 with (TMS)_3SiH and Et_3B. Then the regio- and stereoselective aldol reaction of 7 by using KN(TMS)_2 at 60 ℃ gave rise to the oxygenated steroidal structure 8a as a sole product out of the eight possible steroidal structures 8a〜h. 19-Hydroxy-sarmentgenin (3) was synthesized from 8a. Nine-step sequence from 8a, including deoxygenation of the C7-oxygen functionality and oxidative cleavage of the vinyl ether, resulted in formation of 28. The Cll-ketone of 28 was reduced to the alcohol under the Birch conditions to afford 29 as a single isomer. After the C17-ketone was converted to the vinyl iodide 30, the C17-butenolide was installed by the Cu-accelerated Stale coupling to provide 32. Stereoselective hydrogenation of the C16-17 double bond of 34 generated the desired C17 stereocenter. Finally, the global deprotection delivered the target product 3.

    DOI: 10.24496/tennenyuki.54.0_253

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  105. エイコサペンタエン酸由来の抗炎症性代謝物Resolvin E3の新規同定

    磯部洋輔, 有田誠, 有田誠, 中西広樹, 田口良, 田口良, 占部大介, 井上将行, 新井洋由

    脂質生化学研究   Vol. 54   page: 268 - 271   2012

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  106. α-オキシ炭素ラジカルを用いた分子間C-C結合形成反応の開発

    占部大介, 山口裕樹, 染谷あゆみ, 井上将行

    有機合成シンポジウム講演要旨集   Vol. 101st   2012

  107. α-アルコキシ橋頭位ラジカルを用いた高酸化度炭素環の効率的連結

    山口裕樹, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 132nd ( 2 )   2012

  108. クロトホルボロンの合成研究

    浅羽太郎, 嘉藤裕樹, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 132nd ( 2 )   2012

  109. リアノジンの全合成研究

    長友優典, 田渕俊樹, 占部大介, 井上将行

    日本化学会講演予稿集   Vol. 92nd ( 4 )   2012

  110. リアノジンの不斉合成研究

    枡田健吾, 長友優典, 占部大介, 井上将行

    日本薬学会関東支部大会講演要旨集   Vol. 56th   2012

  111. タラチサミンの全合成研究

    田渕俊樹, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 132nd ( 2 )   2012

  112. レジニフェラトキシンの合成研究

    村井耕一, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 131st ( 2 )   2011

  113. レゾルビンE3の全合成

    轟木秀憲, 増田功嗣, 増田功嗣, 占部大介, 井上将行

    有機合成シンポジウム講演要旨集   Vol. 99th   2011

  114. レゾルビンE3の全合成

    轟木秀憲, 増田功嗣, 増田功嗣, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 131st ( 2 )   2011

  115. Radical-based approach for synthesis of complex natural products

      Vol. 62 ( 8 ) page: 594 - 596   2011

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  116. クロトホルボロンの全合成研究

    嘉藤裕樹, 山下智也, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 131st ( 2 )   2011

  117. カルデノリド類の合成研究

    向井健, 粕谷智史, 占部大介, 井上将行

    有機合成シンポジウム講演要旨集   Vol. 100th   2011

  118. エイコサペンタエン酸由来の抗炎症性代謝物の新規同定

    磯部洋輔, 有田誠, 中西広樹, 田口良, 占部大介, 井上将行, 新井洋由

    次世代を担う若手ファーマ・バイオフォーラム講演要旨集   Vol. 10th   2011

  119. ウアバインの合成研究

    粕谷智史, 占部大介, 井上将行

    日本化学会講演予稿集   Vol. 91st ( 4 )   2011

  120. ウアバインAB環の立体選択的合成

    向井健, 粕谷智史, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 131st ( 2 )   2011

  121. トウセンダニンの合成研究

    青木直人, JAUTZE Sascha, 占部大介, 井上将行

    日本薬学会関東支部大会講演要旨集   Vol. 55th   2011

  122. リアノジンの不斉合成研究

    田渕俊樹, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 131st ( 2 )   2011

  123. レジニフェラトキシンの合成研究

    村井耕一, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 130th ( 2 )   2010

  124. Maresin提出構造の全合成と生物活性

    佐々木健二, 占部大介, 新井由洋, 有田誠, 井上将行

    メディシナルケミストリーシンポジウム講演要旨集   Vol. 29th   2010

  125. クロトフォルボロンの合成研究

    占部大介, 嘉藤裕樹, 山下智也, 井上将行

    複素環化学討論会講演要旨集   Vol. 40th   2010

  126. ウアバインの合成研究

    粕谷智史, 占部大介, 井上将行

    日本化学会講演予稿集   Vol. 90th ( 4 )   2010

  127. アガロフラン骨格を有するセスキテルペンの合成研究

    岩津理史, 占部大介, 井上将行

    日本化学会講演予稿集   Vol. 90th ( 4 )   2010

  128. ハイポニンBの全合成研究

    石山備凡, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 130th ( 2 )   2010

  129. Synthetic Study of Ryanodine

    Nagatomo Masanori, Hagiwara Koji, Tabuchi Toshiki, Urabe Daisuke, Inoue Masayuki

    Symposium on the Chemistry of Natural Products, symposium papers   Vol. 52nd ( 0 ) page: 133 - 138   2010

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    Language:Japanese   Publisher:Symposium on the Chemistry of Natural Products Steering Committee  

    Ryanodine (1) is a potent modulator of the intracellular calcium channels (ryanodine receptors). The highly fused architecture of 1 decorated by the eight tetrasubstituted carbon centers poses a considerable synthetic challenge. In this paper we report an efficient stereoselective synthesis of the pentacyclic ryanodine skeleton. To simplify the synthetic route, we exploited a structural symmetry of the core framework of 1. Thus, the C_2-symmetric core structure 5 was synthesize through the pairwise symmetric functionalizations. Firsrt, C_2-symmetric core structure 5 was synthesized through the pairwise symmetric functionalizations. First, C_2-symmetric bicyclo[2.2.2]octene ring 2, obtained by the dearomatizing Diels-Alder reaction of 2,5-dimethylhydroquinone 8 and maleic anhydride 9, was converted to eight-membered-ring 3 via the two directional ring expansion. Then, the tricyclo[3.3.2.0^<2.6>]decene system was successfully constructed by the newly developed transannular aldol reaction of 14, leading to the key intermediate 5. After desymmetrization of 5 through dihydroxylation, the stereospecific alkylation at sterically hindered C11 position was accomplished by using the highly reactive bridgehead radical generated from thiocarbonate 24, resulting in formation of 25. Regio- and stereoselective C6-allylation from 25, followed by the fing-closing metathesis, provided C-ring of 1. Finally, installation of the C2-isopropenyl group and stereoselective reduction of the C3-ketone afforded 32, which has the pentacycle of ryanodine (1) along with the seven congiguous tetrasubstituted carbon centers.

    DOI: 10.24496/tennenyuki.52.0_133

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  130. リアノジンの全合成研究

    長友優典, 萩原幸司, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 130th ( 2 )   2010

  131. レゾルビンE2の全合成と生物活性

    小川誠治, 占部大介, 横倉良行, 新井洋由, 有田誠, 井上将行

    メディシナルケミストリーシンポジウム講演要旨集   Vol. 28th   2009

  132. Symmetry-Driven Synthesis of ABDE-ring Skeleton of Ryanodine

    萩原幸司, 占部大介, 井上将行

    日本化学会講演予稿集   Vol. 89th ( 2 )   2009

  133. Total Syntheses of Saxitoxin and its Analogues Reviewed

    占部大介

    有機合成化学協会誌   Vol. 67 ( 3 ) page: 248 - 249   2009

  134. ウアバインの合成研究

    粕谷智史, 占部大介, 井上将行

    有機合成化学セミナー講演予稿集   Vol. 26th   2009

  135. アガロフラン骨格を有するセスキテルペンの全合成研究

    岩津理史, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 129th ( 2 )   2009

  136. O,S-アセタールを鍵中間体とする炭素骨格構築法の開発

    染谷あゆみ, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 129th ( 2 )   2009

  137. Hyponine Bの合成研究

    石山備凡, 占部大介, 井上将行

    日本薬学会年会要旨集   Vol. 129th ( 2 )   2009

  138. 強力な抗腫瘍活性を有するハリコンドリンB類縁体の合成研究

    占部大介, 鏑木洋介, 岸義人

    次世代を担う有機化学シンポジウム講演要旨集   Vol. 6th   2008

  139. リアノジンの合成研究

    萩原幸司, 岩津理史, 金野大助, 友田修司, 占部大介, 井上将行

    有機合成シンポジウム講演要旨集   Vol. 94th   2008

  140. 強力な抗腫瘍活性を有する海洋天然物ハリコンドリン類の実用的合成法の開発

    鏑木洋介, 難波康祐, 占部大介, 岸義人

    有機合成シンポジウム講演要旨集   Vol. 92nd   2007

  141. Halichondrins, Anti-tumor Marine Natural Products: Development of Practical Synthesis

    Kaburagi Yosuke, Namba Kosuke, Urabe Daisuke, Kishi Yoshito

    Proceedings of the Symposium on Progress in Organic Reactions and Syntheses   Vol. 33rd ( 0 ) page: 5 - 5   2007

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    Language:Japanese   Publisher:Division of Organic Chemistry, The Pharmaceutical Society of Japan  

    Halichondrin B (HB) has received much attention due to its intriguing structure and extraordinary <I>in vitro</I> and <I>in vivo</I> antitumor activity. E7389 is a fully synthetic macrocyclic ketone analog of HB, with antitumor activity matching or even surpassing those of HB. Since the first and only total synthesis of HB in 1992, the continuing effort of our group is to establish a practical synthesis to HB (particularly right half of HB, which exhibits the same antitumor activity as HB) and E7389. This presentation will report recent progress toward practical synthesis toward this aim:<BR>(1) Catalytic asymmetric Ni/Cr coupling reaction at C26-C27.<BR>(2) Catalytic Ni/Cr macrocyclization without use of high dilution conditions.<BR>(3) Use of ion-exchange resins for workup of TBAF-mediated desilylation reaction and ketal formation.<BR>(4) Selective ammonolysis reaction of terminal epoxide.

    DOI: 10.14895/hannou.33.0.5.0

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  142. P-52 Synthesis of Tetrodotoxin and its Analogues Based on Multifunctionality of Trichloroacetamide

    Nishikawa T., Urabe D., Koide Y., Tomita M., Tsujimoto T., Isobe M.

    International Symposium on the Chemistry of Natural Products   Vol. 2006 ( 0 ) page: _P-52_ - 52"   2006

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    Language:English   Publisher:the Science Council of Japan under the Auspices of the International Union of Pure and Applied Chemistry  

    DOI: 10.24496/intnaturalprod.2006.0__p-52_

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  143. パナマ産ヤドクガエルの毒ゼテキトキシンの全合成研究

    占部大介, 西川俊夫, 西川俊夫, 磯部稔

    日本農芸化学会大会講演要旨集   Vol. 2006   2006

  144. 抗腫よう性抗生物質パクタマイシンの合成研究

    辻本恭, 西川俊夫, 西川俊夫, 占部大介, 磯部稔

    日本農芸化学会大会講演要旨集   Vol. 2005   2005

  145. トリクロロアセトアミドの新規脱保護反応に関する研究

    杉野公美, 占部大介, 西川俊夫, 磯部稔

    日本農芸化学会大会講演要旨集   Vol. 2005   2005

  146. ヤドクガエルの毒ゼテキトキシンのN-アシルイソオキサゾリジン部分のモデル化合物の合成

    占部大介, 西川俊夫, 西川俊夫, 磯部稔

    日本農芸化学会大会講演要旨集   Vol. 2005   2005

  147. デオキシテトロドトキシン類の合成経路を基にしたフグ毒テトロドトキシンの全合成研究

    占部大介, 西川俊夫, 磯部稔

    日本農芸化学会大会講演要旨集   Vol. 2004   2004

  148. フグ毒テトロドトキシンの効率的不斉全合成

    占部大介, 西川俊夫, 磯部稔

    天然有機化合物討論会講演要旨集   Vol. 46th   2004

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KAKENHI (Grants-in-Aid for Scientific Research) 9

  1. 計算化学に基づく高精度合成計画法の開発と複雑天然物のコンピューター支援全合成

    Grant number:22K18340  2022.6 - 2028.3

    科学研究費助成事業  挑戦的研究(開拓)

    占部 大介

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\26000000 ( Direct Cost: \20000000 、 Indirect Cost:\6000000 )

    本研究では、創薬リードとなりうる生物活性複雑中分子(天然物)の革新的な合成供給単純化を目指し、有機合成化学と計算化学を基盤とした高精度合成計画プログラムの構築とその計画に基づいた複雑天然物のコンピューター支援全合成を実施する。具体的には、1.半自動遷移状態探索プログラムの作成、2.コンピューター上での反応最適化法の確立、3.超複雑天然物のコンピューター支援全合成を実施する。
    前年度までに、半自動遷移状態探索プログラムの拡張とそれを用いたアゲリフェリンの全合成に成功した。この結果から、Diels-Alder反応などのペリ環状反応は本プログラムと相性が良く、高精度で反応予測が可能であることが分かった。本年度は、[3,3]-シグマトロピー反応に本プログラムを適用し、第4級炭素構築を伴うベンゼンの脱芳香族化反応の開発を行った。
    極性官能基などで活性化されていない単純なベンゼンはその安定性から、脱芳香族化を伴うアルキル化に過酷な条件が必要とされる。実際に、オルト位にメチルを有するベンゼンのClaisen転位を半自動遷移状態探索プログラムを用いて評価したが、極めて高い活性化エネルギーを要し、また生成物が不安定性されることから反応の進行は見込めないことが分かった。一方で、イノール構造を利用したMeinhan-Claisen転位は低い活性化エネルギーと生成物の安定性から、進行が見込めることが分かった。計算化学によって設計した分子を合成し、[3,3]-シグマトロピー反応を行ったところ、予想通り第4級炭素構築を伴うベンゼンの脱芳香族化が進行した。この反応はこの段階では停止せず、さらに環化とメチル基の転位を引き起こし、第4級炭素構築を有するインダノン化合物を予期せず与えた。
    以上の結果から、予想外の連続反応が進行したものの、半自動遷移状態探索プログラムによって脱芳香族化を伴う[3,3]-シグマトロピー反応を設計することができた。
    本年度は、これまでに開発した半自動遷移状態探索プログラムを用いて、困難とされている第4級炭素構築を伴うベンゼンの脱芳香族化反応を設計し、実際に実験によってその進行を確認した。前年度に自死した全合成へのプログラム応用とともに、反応開発にも本プログラムが適用できることを示す事ができており、研究は概ね順調に進展していると言える。
    半自動遷移状態探索プログラムの拡張に向けて、イオン反応や遷移金属反応の遷移状態探索を検討し、その課題点や適用可能性を探る。また、アゲリフェリン以外の2-アミノイミダゾール天然物の合成、ペリ環状反応以外にも本プログラムを適用し、その有用性を実証する。

  2. Study toward Rational Simplification of on Polyketides and Creation of Bioactive Molecules

    Grant number:20H03366  2020.4 - 2024.3

    Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    Urabe Daisuke

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\17810000 ( Direct Cost: \13700000 、 Indirect Cost:\4110000 )

    Polyketides are attractive leads for drug development because of their diverse structures and biological activities. On the other hand, structural modification, especially simplification, of bioactive natural products, toward drug discovery, is difficult, and no rational standard process has been established. In this study, three rare polyketides were selected as targets for developing rational process for simplification of structures focusing on their unique conformations. When the study was started , the structures of the three polyketides had not been fully elucidated. Therefore, the structures of formosalide A and amphidinolide L were estimated by NMR calculations. Synthetic studies of the deduced structures led to establishment of the efficient synthetic route to the C1-C18 fragment of formosalide A and the C20-C26 fragment of amphidinolide L.

  3. A study toward total synthesis of complex triterpenoids by using chemoselective radical couplings as key transformations

    Grant number:16H06213  2016.4 - 2020.3

    Grants-in-Aid for Scientific Research  Grant-in-Aid for Young Scientists (A)

    Urabe Daisuke

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\25090000 ( Direct Cost: \19300000 、 Indirect Cost:\5790000 )

    Medium-molecule natural products that has the advantages of both small- and large-molecular drugs have attracted attention as a next-generation post-biomedicine. In this project, we carried out the studies toward establishment of synthetic routes of three triterpenoids, batrachotoxin, nakiterpiosin, and veratridine, and their natural and unnatural analogs by using chemoselective radical couplings as key transformations. In the synthetic study of batrachotoxin, the radical coupling of highly functionalized fragments was developed to realize a construction of the steroid skeleton. In the synthetic studies of nakiterpiosin and veratridine, advanced intermediates for the key radical couplings were synthesized.

  4. Development and Application of Convergent Strategies for Unified Total Syntheses of Architecturally Complex Natural Products

    Grant number:26253003  2014.4 - 2017.3

    Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (A)

    Inoue Masayuki, URABE Daisuke, NAGATOMO Masanori, TAKEFUMI Kuranaga

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    Authorship:Collaborating Investigator(s) (not designated on Grant-in-Aid)  Grant type:Competitive

    Architecturally complex and densely oxygenated natural products often have potent and selective biological activities. In this study, we focused on efficient, practical and flexible syntheses of these natural products based on radical chemistry. We developed an a-alkoxy radical methodology for assembly of two- and three components, and efficient radical-radical homo- and heterocoupling reactions of a-alkoxy radicals. By taking advantage of these strategies, we realized the total syntheses of various complex natural products, including ryanodine, crotophorbolone, 4-hydroxyzinowol, oubagenin, and zaragozic acid C. Moreover, these synthetic routes were applied to unified preparation of the structurally related compounds for the future structure-activity relationship studies. Because of the broadness of the reaction scope and the mildness of the conditions, these powerful strategies introduce novel technologies for expedited total synthesis of densely oxygenated natural products.

  5. 抗がん活性を有する非天然ブファジエノリドの創製

    Grant number:26102716  2014.4 - 2016.3

    科学研究費助成事業  新学術領域研究(研究領域提案型)

    占部 大介

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\5720000 ( Direct Cost: \4400000 、 Indirect Cost:\1320000 )

    平成27年度は、既に確立している収束的合成経路に従って、糖を有するカルデノリドとして19-ヒドロキシサルメントゲニンラムノシド、ブリオフィリンCの類縁体となる非天然型ブファジエノリド、C17-エピブリオフィリンCの2つの化合物を合成する事に成功した。具体的には、既に合成を完了している19-ヒドロキシサルメントゲニンから、第一級ヒドロキシ基をブロモベンゾエート、第二級ヒドロキシ基をアセテートとして保護した後、トリクロロアセトイミデートを脱離基として有しヒドロキシ基をベンゾエートとして保護したラムノース誘導体とのグリコシル化により、糖を導入した。その後、全ての保護基を塩基性条件下にて除去し、19-ヒドロキシサルメントゲニンラムノシドを合成した。また、前年度までに確立した方法によりブリオフィリンCの骨格を構築した後、C16-17二重結合を水素添加によって還元した。次いで、ヒドロキシ基の保護基として用いたTBS基を除去し、C17-エピブリオフィリンCを合成した。還元の立体選択性を逆転させてブリオフィリンCを合成する事を目的とし、アンドロステロンから容易に導ける化合物を用いて、モデル研究を行った。既にWisnerらによって報告されている結果を基にして、ピロン等価体であるフランを導入してC16-17二重結合を水素添加したところ、望む立体選択性で反応が進行する事が分かった。これによって、ブリオフィリンCの合成につながる知見を得ることができた。
    27年度が最終年度であるため、記入しない。
    27年度が最終年度であるため、記入しない。

  6. Development of the stereocontrolled synthesis of the highly oxygenated steroids

    Grant number:25460007  2013.4 - 2016.3

    Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    Urabe Daisuke

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    Authorship:Principal investigator 

    Grant amount:\5200000 ( Direct Cost: \4000000 、 Indirect Cost:\1200000 )

    In this research project, we have established the strategy for the divergent synthesis of the highly oxygenated steroid compounds. The stereocontrolled synthesis of the core system of the steroid has been developed by the convergent radical coupling of the diverse AB-rings and the D-ring and the following stereoselective intramolecular aldol reaction. Based on the developed method, the total synthesis of complex natural product ouabagenin has been achieved. Furthermore, the intermediate towards toosendanine has been synthesized.

  7. Synthetic study of highly oxygenated diterpenes based on the bridgehead radical reaction

    Grant number:23790005  2011 - 2012

    Grants-in-Aid for Scientific Research  Grant-in-Aid for Young Scientists (B)

    URABE Daisuke

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\4420000 ( Direct Cost: \3400000 、 Indirect Cost:\1020000 )

    The C-C bond formation utilizing an alkoxy bridgehead carbon radical was developed. The high reactivity of the radical species realized the congested C-C bond formation to connect oxygenated carbocycles by two- and three-component reactions. Based on the strategy, the5/7/6-fused carbocycles of crotophorbolone, a tigliane diterpene, was successfully assembled in a stereoselective fashion.

  8. Development of efficient synthetic method of functionalized carbocycles and synthetic study of resiniferatoxin

    Grant number:20890043  2008 - 2009

    Grants-in-Aid for Scientific Research  Grant-in-Aid for Young Scientists (Start-up)

    URABE Daisuke

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\2925000 ( Direct Cost: \2250000 、 Indirect Cost:\675000 )

    An efficient radical cyclization from alkoxy selenoacetals, prepared by seleno pummerer reaction, was successfully developed to provide functionalized carbocycles. Toward a total synthesis of resiniferatoxin featured by the radical reaction, an advanced intermediate was synthesized from the quinone derivative through Diels-Alder reaction.

  9. パナマ産ヤドクガエルの毒ゼテキトキシンの全合成研究

    Grant number:05J07704  2005 - 2006

    日本学術振興会  科学研究費助成事業 特別研究員奨励費  特別研究員奨励費

    占部 大介

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    アリルアルコールとトリクロロアセトニトリルから容易に調製できるアリルトリクロロアセトイミデートのアリルトリクロロアセトアミドへの転位反応は窒素官能基の導入法として有用な反応である.しかし、転位成績体のトリクロロアセトアミドのアミンへの脱保護には通常のアミド加水分解の条件が広く用いられていた.本研究室ではこれまでに、トリクロロアセトアミドをDMF中、炭酸セシウムと加熱すると、アミドの加水分解条件では不安定な官能基を有する基質に対しても高収率でアミンへと脱保護できる事を報告している.今回、本反応の反応機構を解析し中間体としてイソシアナートが生成している事を見いだし、温和な条件で除去可能な既知のアミノ基の保護基へとトリクロロアセトアミドを変換する方法へと展開した.すなわち、トリクロロアセトアミドをDMF中で炭酸ナトリウムと加熱すると高収率で得られるイソシアナートに対しワンポットで塩化銅(I)及び各種アルコールを添加し、Cbz, Troc, Alloc, Boc, Teoc, Fmocに高収率で変換することに成功した.
    2006年5月からはハーバード大学化学・生物化学科の岸義人教授のもとに渡航し研究を行った.岸教授は、Ni、Crを用いたアルデヒドとアルケニルハライド類との汎用性の高いカップリング反応を用いた生理活性物質の全合成を展開している.さらに近年では触媒効率の高いNi錯体、不斉誘起の高いCrの配位子を見いだし、反応後のCrの効率的な再生を可能にすることで、触媒的不斉Ni、Crカップリング反応を発展させている.今回岸教授のもとで、強力な抗腫瘍活性を有するハリコンドリン類の合成研究に従事し、その過程で本カップリング反応を様々な基質に対して高立体選択的に進行させるためのCr配位子選択法について検討した.Cr配位子は高い多様性を有するため本来は個々の基質に対し配位子の最適化を行う必要があると考えられるが、Ni、Crカップリング反応における立体選択性はCr配位子のサイズを大きくするほど高くなる場合と、小さくするほど高くなる場合の2パターンがある事が分かった.このことから高い多様性を有するCr配位子の選択を容易にする事ができた.

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Teaching Experience (On-campus) 1

  1. 有機化学4

    2026

Teaching Experience (Off-campus) 12

  1. 応用化学部門

    2021.4 - 2022.3 Tokyo University of Agriculture and Technology)

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    Level:Postgraduate 

  2. 生命科学史

    2017.4 - 2026.3 Toyama Prefectural University)

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    Level:Undergraduate (specialized) 

  3. 生物有機化学

    2017.4 - 2026.3 Toyama Prefectural University)

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    Level:Postgraduate 

  4. 生物工学特別研究

    2017.4 - 2026.3 Toyama Prefectural University)

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    Level:Postgraduate 

  5. 生物工学特別演習

    2017.4 - 2026.3 Toyama Prefectural University)

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    Level:Postgraduate 

  6. 卒業研究2

    2017.4 - 2026.3 Toyama Prefectural University)

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    Level:Undergraduate (specialized) 

  7. 有機化学4

    2017.4 - 2026.3 Toyama Prefectural University)

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    Level:Undergraduate (specialized) 

  8. 卒業研究1

    2017.4 - 2026.3 Toyama Prefectural University)

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    Level:Undergraduate (specialized) 

  9. 有機化学実験

    2017.4 - 2026.3 Toyama Prefectural University)

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    Level:Undergraduate (specialized) 

  10. 有機化学演習

    2017.4 - 2026.3 Toyama Prefectural University)

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    Level:Undergraduate (specialized) 

  11. 有機反応化学

    2015.4 - 2016.3 The University of Tokyo)

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    Level:Undergraduate (liberal arts) 

  12. 薬学実習I

    2008.1 - 2016.3 The University of Tokyo)

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    Level:Undergraduate (specialized) 

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Academic Activities 5

  1. 日本農芸化学会中部支部幹

    Role(s):Planning, management, etc.

    2024.4 - 2026.3

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    Type:Academic society, research group, etc. 

  2. 日本農芸化学会2021年度大会シンポジウム世話人代表

    Role(s):Planning, management, etc.

    2021.4 - 2022.3

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    Type:Competition, symposium, etc. 

  3. くすりのシリコンバレーTOYAMA」創造コンソーシアム 富山県立大学サマースクール<製薬工学コース(分析・製剤・バイオ医薬)>

    Role(s):Planning, management, etc.

    2020.4 - 2021.4

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    Type:Competition, symposium, etc. 

  4. 有機合成化学協会誌編集委員

    Role(s):Planning, management, etc.

    2017.4 - 2019.3

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    Type:Academic society, research group, etc. 

  5. 次世代を担う有機化学シンポジウム世話人

    Role(s):Planning, management, etc.

    2013.4 - 2015.3

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    Type:Competition, symposium, etc.