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Development of a method for the preparation of optically active tetrasubstituted allenes via dynamic kinetic resolution: its application to syntheses of natural products

Research Project

Project/Area Number 15K07864
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionUniversity of Shizuoka

Principal Investigator

Egi Masahiro  静岡県立大学, 食品栄養科学部, 教授 (80363901)

Co-Investigator(Kenkyū-buntansha) 菅 敏幸  静岡県立大学, 薬学部, 教授 (10221904)
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsアレン / 天然物合成 / 有機合成化学 / プロパルギルアルコール / シグマトロピー転位 / 分子内環化 / インデン / 触媒 / イナミド / 天然物 / 全合成 / 選択的還元 / 動的光学分割
Outline of Final Research Achievements

Our efficient synthesis of tetrasubstituted allenes was applied to total synthetic studies on natural products. In the synthesis of raputindole A, the allene obtained underwent the intramolecular cyclization to give the tricyclic skeleton. Chelation-controlled reduction was carried out, followed by the introduction of side chains to access raputindole A. Moreover, tetrasubstituted allene was synthesized as a key intermediate toward the total synthesis of taiwaniaquinol D.
In order to develop a synthesis of optically active tetrasubstituted allenes using dynamic kinetic resolution, a racemization catalyst of propargyl alcohols and a chiral silver catalyst that catalyzes sigmatropic rearrangement were investigated.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (2 results)

All 2018

All Presentation (2 results)

  • [Presentation] Raputindole Aの合成研究2018

    • Author(s)
      中野広暁、神谷真鈴、菅敏幸、江木正浩
    • Organizer
      第19回静岡ライフサイエンスシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] ラプチンドールAの全合成研究2018

    • Author(s)
      中野広暁、神谷真鈴、菅敏幸、江木正浩
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report

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Published: 2015-04-16   Modified: 2019-03-29  

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