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Development of efficient synthetic method of tricyclic humulanolides and structure-activity relationship

Research Project

Project/Area Number 17K08222
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionJapan Women's University

Principal Investigator

ABE Hideki  日本女子大学, 理学部, 教授 (00328551)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2019: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords三環性フムラノライド / wilfolide B / ラジカル環化反応 / 異性化反応 / 閉環メタセシス / 類縁体 / Knoevenagel 縮合 / フムラノライド類 / 全合成
Outline of Final Research Achievements

With the aim of studying the structure-activity relationship of humulene-based tricyclic fumulanolides, development of an efficient synthetic method for them. After synthesizing an aldehyde having a Z-unsaturated ester from 2,2-dimethyl-1,3-propanediol as a starting material, the radical cyclization using samarium iodide afforded the bicyclic lactone. Then, two types of side chains were constructed for the bicyclic lactone via introduction of a butenyl group at the lactone carbonyl α position, and an isomerization was performed to adjust the stereochemistry. Finally, the construction of the 8-membered ring by ring closing metathesis followed by catalytic hydrogenation allowed us to achieve the first total synthesis of wilfolide B.

Academic Significance and Societal Importance of the Research Achievements

今回確立した三環性フムラノライド wilfolide B の全合成経路は、類似した三環性化合物の合成を可能とするため、今後構造活性相関研究への展開を期待させる成果が得られたものと考えている。またそこから生まれる新しい知見は、フムラノライド類の利用価値を判別するための材料の1つになるものと思われることから、今回の成果は非常に意義深い成果であると考えられる。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (3 results)

All 2019 2018

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (2 results)

  • [Journal Article] Total synthesis of the tricyclic humulanolide wilfolide B2019

    • Author(s)
      Abe Hideki、Sato Saki、Oishi Wakana、Tamura Mei、Kobayashi Toyoharu、Ito Hisanaka
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 31 Pages: 2059-2062

    • DOI

      10.1016/j.tetlet.2019.06.058

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Presentation] 三環性フムラノライド Wilfolide B の全合成2019

    • Author(s)
      佐藤咲、阿部秀樹、田村芽生、小林豊晴、伊藤久央
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 三環性フムラノライド Wilfolide B の合成研究2018

    • Author(s)
      佐藤咲、阿部秀樹、大石若奈、小林豊晴、伊藤久央
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report

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Published: 2017-04-28   Modified: 2021-02-19  

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