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Synthetic Study of Azaspiracid

Research Project

Project/Area Number 20710160
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Living organism molecular science
Research InstitutionHokkaido University

Principal Investigator

YOSHIMURA Fumihiko  Hokkaido University, 大学院・理学研究院, 助教 (70374189)

Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2009: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2008: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsアザスピラシド / スピロ化合物 / アルコキシスタナン / 立体選択的反応 / 海産毒 / 光学活性カルバニオン / 置換反応 / 不斉アシル化 / 全合成研究
Research Abstract

During the synthetic studies toward the total synthesis of Azaspiracid, a marine toxin possessing unique molecular structure with stereochemical complexity, the following key synthetic methods were established. (1) A practical synthetic method for optically active α-hydroxystannane derivatives has been developed by kinetic resolution of secondary α-hydroxystannanes via asymmetric acylation reaction by using the Oriyama's chiral diamine catalyst followed by acetalization of the unreacted alcohol as a MOM-ether in one-pot. (2) A novel and efficient synthetic method for the construction of the bicyclic FG-ring moiety has been developed by using Fe(TPP)OTf-catalyzed sequential isomerization-acetalyzation reaction.

Report

(3 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • Research Products

    (7 results)

All 2009 2008

All Journal Article (7 results) (of which Peer Reviewed: 7 results)

  • [Journal Article] Total Synthesis of Zoanthenol2009

    • Author(s)
      Takahashi, Y; Yoshimura, F.; Tanino, K.; Miyashita, M.
    • Journal Title

      Angewandte Chemie International Edition 48巻

      Pages: 8905-8908

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthetic Studies of the Zoanthamine Alkaloids: The Total Synthesis of Norzoanthamine and Zoanthamine2009

    • Author(s)
      Yoshimura, F.; Sasaki, M.; Hattori, I.; Komatsu, K.; Sakai, M.; Tanino, K.; Miyashita, M.
    • Journal Title

      Chemistry-A European Journal 15巻

      Pages: 6626-6644

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective SN2' alkylation reaction sequence of theγ, δ-epoxyα, β-unsaturated ester system viaγ, δ-chlorohydrin intermediates by the use of a R3Al-CuCN reagent2009

    • Author(s)
      Yoshimura, F.; Matsui, A.; Hirai, A.; Tanino, K.; Miyashita, M.
    • Journal Title

      Tetrahedron Letters 50巻

      Pages: 5126-5129

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] An Efficient Synthetic Method for 3-Bromofuran Derivatives via Stereoselective Cyclization ofγ, δ-Epoxy-(E)-α-bromoacrylates2009

    • Author(s)
      Yoshimura, F.; Takahashi, M.; Tanino, K.; Miyashita, M.
    • Journal Title

      Heterocycles 77巻

      Pages: 201-206

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereospecific interconversion of cis- and trans-γ, δ-epoxyα, β-unsaturated ester systems2008

    • Author(s)
      Yu, X.; Yoshimura, F.; Tanino, K.; Miyashita, M.
    • Journal Title

      Tetrahedron Letters 49巻

      Pages: 7442-7445

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereospecific epoxide-opening reactions of 1, 1 -dibromo-3, 4-epoxy-1-alkenes with carbon nucleophiles2008

    • Author(s)
      Yoshimura, F.; Takahashi, M.; Tanino, K.; Miyashita, M.
    • Journal Title

      Tetrahedron Letters 49巻

      Pages: 6991-6994

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Stereospecific Substitution of α, β-Unsaturatedγ, δ-Epoxy Esters by Alcohols with Double Inversion of Configuration: Synthesis of 4-Alkoxy-5-hydroxy-2-pentenoates2008

    • Author(s)
      Yu, X.; Yoshimura, F.; Ito, F.; Sasaki, M.; Hirai, A.; Tanino, K.; Miyashita, M.
    • Journal Title

      Angewandte Chemie International Edition 47巻

      Pages: 750-754

    • Related Report
      2009 Final Research Report
    • Peer Reviewed

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Published: 2008-04-01   Modified: 2016-04-21  

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