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Synthetic studies on amphidinolide N by using Organocatalyst

Research Project

Project/Area Number 18K14206
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionTohoku University

Principal Investigator

Umemiya Shigenobu  東北大学, 理学研究科, 助教 (10802754)

Project Period (FY) 2018-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords全合成 / 不斉合成 / マクロリド / 天然物 / 構造決定 / 生物活性 / 有機触媒 / 不斉アルドール反応 / 天然物化学
Outline of Final Research Achievements

Amphidinolides are a series of cytotoxic natural products isolated from the symbiotic dinoflagellates of the genus Amphidinium. In this research, a scalable and enantioselective total synthesis of amphidinolide N was achieved in 31 longest liner steps. The C1-C13 fragment of amphidinolide N was prepared in multi-gram scale by using the asymmetric cross aldol reaction of ethyl glyoxylate with aldehydes catalyzed by diarylprolinol as a key step. Detailed NMR experiments of the synthetic amphidinolide N disclosed that our synthetic product is not identical with the proposed structure by Kobayashi. Comparison of 13C NMR chemical shift differences between the synthetic and natural product suggested that the proposed structure would be incorrect regarding to the stereochemistry around C15.

Academic Significance and Societal Importance of the Research Achievements

今回の合成標的であるamphidinolide Nは、その強力な生物活性からこれまでに世界中の研究グループで合成競争が行われていた化合物である。しかし、今日に至るまで、全合成の報告例はなかった。唯一当研究室での類縁体の合成報告があるものの、その供給の難しさから最終生成物のスペクトルデータを集めることは困難だった。今回、合成戦略を変えることで化合物の量的供給に成功した。これにより現在まで困難だった、本化合物を使った生物学的研究が実施できるようになった。

Report

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

    (1 results)

All 2018

All Presentation (1 results)

  • [Presentation] 超強力な抗腫瘍活性を有するamphidinolide Nの合成研究2018

    • Author(s)
      ○田渡司、梅宮茂伸、林雄二郎
    • Organizer
      有機合成化学セミナー
    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2021-02-19  

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