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Synthetic Studies of Marine Polyketide Ascospiroketal including 5, 5-Spiroketal Moiety

Research Project

Project/Area Number 23590016
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionTokyo University of Pharmacy and Life Science

Principal Investigator

MIYAOKA Hiroaki  東京薬科大学, 薬学部, 准教授 (10231622)

Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2012: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2011: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords合成化学 / 薬学 / スピロケタール / ポリケチド / アスコスピロケタール
Research Abstract

Ascospiroketal A is a marine polyketide having specific tricyclic skeleton including tetrahydrofuran and 5,5-spiroketal.Sufone derivative, segment C7-C11, was synthesized from D-(+)-malic acid by 9 steps. Alkyl iodide derivative, segment C1-C6, was synthesized from L-(+)-tartaric acid by 12 steps. 5,5-Spiroketal segment was synthesized by combination of segment C7-C11 and segment C1-C6 and then the removal of 1,3-dithiane and the protecting group of hydroxy groups. Synthesis of tricyclic segment including tetrahydrofuran ring was successfully carried out by construction of quaternary asymmetric carbon and intramolecular etherification. Total synthesis of ascospiroketal A is currently under way by connection of the tricyclic segment and C12-C16 segment.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (4 results)

All 2013 2011 Other

All Presentation (3 results) Remarks (1 results)

  • [Presentation] 海洋性真菌由来の三環性ポリケチドAscospiroketal Aの合成研究2013

    • Author(s)
      原善偉、長田遼、荒川航人、本多達也、川島悦子、宮岡宏明
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2013 Final Research Report
  • [Presentation] 海洋性真菌由来の三環性ポリケチドAscospiroketal Aの合成研究2013

    • Author(s)
      原 善偉,長田 遼,荒川航人,本多達也,川島悦子,宮岡宏明
    • Organizer
      日本薬学会 第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] Ascospiroketal Aの合成研究2011

    • Author(s)
      荒川航人、本多達也、川島悦子、宮岡宏明
    • Organizer
      日本薬学会第131年会
    • Place of Presentation
      静岡
    • Related Report
      2013 Final Research Report
  • [Remarks]

    • URL

      http://woden.ps.toyaku.ac.jp/~otak/index.html

    • Related Report
      2013 Final Research Report

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Published: 2011-08-05   Modified: 2019-07-29  

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