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Synthetic approach directed toward the determination of the stereochemistry of scarce natural products with potent antimitotic or cytotoxic activity

Research Project

Project/Area Number 24658105
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionTohoku University

Principal Investigator

KUWAHARA Shigefumi  東北大学, (連合)農学研究科(研究院), 教授 (30170145)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsnigricanoside / amphidinolide / cytotoxic / antimitotic / glycolipid / macrolide / topsentolide / oxylipin / 細胞毒性
Research Abstract

Toward the determination of the stereochemistry of nigricanoside A, a marine-derived glycolipid bearing an unprecedented structural pattern and a potent antimitotic activity, the synthesis of its highly oxygenated alpha- and beta-fatty acid chains has been accomplished. Its southeastern segment consisting of a galactosyl glycerol unit and the right-hand portion of the bata-chain has also been synthesized. The segment is planned to connect with a northwestern segment of the target molecule by the Julia-Kocienski coupling reaction. Synthetic study on the 26-membered macrolide amphidinolide N has also been undertaken and the preparation of its C7-C13 portion has been completed by using an asymmetric vinylogous Mukaiyama aldol reaction (Kobayashi aldol reaction) as the key step.

Report

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

    (11 results)

All 2014 2013 2012 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (6 results) Remarks (1 results)

  • [Journal Article] Synthesis of topsentolides A_2 and C_2, and non-enzymatic conversion of the former to the latter2014

    • Author(s)
      Ryo Towada, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron

      Volume: vol. 70(in press) Issue: 24 Pages: 6878-6881

    • DOI

      10.1016/j.tet.2014.04.040

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter2014

    • Author(s)
      Ryo Towada, Shigefumi Kuwahara
    • Journal Title

      Tetrahedron

      Volume: 70

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereochemical assignment of topsentolide C_2 by stereodivergent synthesis of its four diastereomers2013

    • Author(s)
      R. Towada, Y. Kurashina, S. Kuwahara
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 50 Pages: 6878-6881

    • DOI

      10.1016/j.tetlet.2013.10.032

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of a Protected Form of (6<I>R</I>,7<I>E</I>,9<I>S</I>,10<I>R</I>,12<I>Z</I>)-6,9,10-Trihydroxy-7,12-hexadecadienoic Acid2012

    • Author(s)
      Yusuke Kurashina, Shigefumi Kuwahara
    • Journal Title

      Bioscience, Biotechnology, and Biochemistry

      Volume: 76 Issue: 3 Pages: 605-607

    • DOI

      10.1271/bbb.110829

    • NAID

      10030751045

    • ISSN
      0916-8451, 1347-6947
    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Presentation] topsentolide C_2およびA_2の合成研究2014

    • Author(s)
      十和田諒,倉科友輔,桑原重文
    • Organizer
      日本農芸化学会2014年度大会
    • Place of Presentation
      明治大学生田キャンパス
    • Year and Date
      2014-03-29
    • Related Report
      2013 Final Research Report
  • [Presentation] topsentolide C2およびA2の合成研究2014

    • Author(s)
      十和田諒,倉科友輔,桑原重文
    • Organizer
      日本農芸化学会2014年度大会
    • Place of Presentation
      明治大学生田キャンパス
    • Related Report
      2013 Annual Research Report
  • [Presentation] Nigricanoside類の絶対立体配置決定にむけた合成研究2013

    • Author(s)
      倉科友輔,十和田諒,桑原重文
    • Organizer
      日本農芸化学会東北支部第148回大会
    • Place of Presentation
      岩手大学農学部
    • Year and Date
      2013-10-26
    • Related Report
      2013 Final Research Report
  • [Presentation] 細胞毒性を有する酸化型不飽和脂肪酸ラクトンtopsentolide C_2の合成研究2013

    • Author(s)
      十和田諒,倉科友輔,桑原重文
    • Organizer
      日本農芸化学会東北支部第148回大会
    • Place of Presentation
      岩手大学農学部
    • Year and Date
      2013-10-26
    • Related Report
      2013 Final Research Report
  • [Presentation] 細胞毒性を有する酸化型不飽和脂肪酸ラクトンtopsentolide C2 の合成研究2013

    • Author(s)
      十和田諒,倉科友輔,桑原重文
    • Organizer
      日本農芸化学会東北支部第148回大会
    • Place of Presentation
      岩手大学農学部
    • Related Report
      2013 Annual Research Report
  • [Presentation] Nigricanoside 類の絶対立体配置決定にむけた合成研究2013

    • Author(s)
      倉科友輔,十和田諒,桑原重文
    • Organizer
      日本農芸化学会東北支部第148回大会
    • Place of Presentation
      岩手大学農学部
    • Related Report
      2013 Annual Research Report
  • [Remarks] 生物有機化学分野ホームページ

    • URL

      http://www.agri.tohoku.ac.jp/yuuki/index-j.html

    • Related Report
      2013 Annual Research Report

URL: 

Published: 2013-05-31   Modified: 2019-07-29  

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