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1998 Fiscal Year Final Research Report Summary

New Synthetic Method for Biologically Active Diterpeniods

Research Project

Project/Area Number 09680562
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionHOKKAIDO UNIVERSITY

Principal Investigator

MATSUDA Fuyuhiko  Grad.School of Environmental Earth Science, Hokkaido Univ., Associate Professor, 大学院・地球環境科学研究科, 助教授 (10219446)

Project Period (FY) 1997 – 1998
KeywordsDiterepene / Vinigrol / Neighboring Group Participation / 8-Membered Ring / Samarium (II) Iodide / Total Synthesis
Research Abstract

A unique class of highly oxygenated diterpenoids represented by grayanotoxin and vinigrol has been exhibited remarkable physiological activity. Their remarkable physiological activity and complicated structure pose these molecules as very challenging targets for total synthesis. We have demonstrated the powerful influence of appropriately positioned hydroxyl groups in controlling the stereochemical outcome of the SmI2-mediated reductive couplings. In all cases of these hydroxyl-directed transformations, excellent diastereoselectivity was achieved. The impact which this new methodology on synthetic organic chemistry has is clearly evident from its applicability to total synthesis, one notable example being grayanotoxin. Furthermore, it was found that the introduction of a conformational constrain greatly enhances the ability of acyclic precursors to undergo SmI2-promoted reductive cyclization of medium rings. The 8-6 fused ring system of vinigrol was synthesized through the efficient cyclization of the 8-membered ring using an SmI_2-induced coupling.

  • Research Products

    (6 results)

All Other

All Publications (6 results)

  • [Publications] F.Matsuda: "Convenient Cyclization of Medium Rings Using SmI_2" Tetrahedron Lett.39. 863-864 (1998)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] F.Matsuda: "Hydroxyl-Directed Couplings Promoted by SmI_2" Chem.Eur.J.5(印刷中). (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] F.Matsuda: "Urethane Group Directed Couplings Mediated by SmI_2" J.Chem.Soc., Perkin Trans.1. 印刷中. (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] F.Matsuda: "Convenient Cyclization of Medium Rings Using SmI_2" Tetrahedron Lett.39 (8). 863-864 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] F.Matsuda: "Hydroxyl-Directed Couplings Promoted by SmI_2" Chem.Eur.J.5 (in press). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] F.Matsuda: "Urethane Group Directed Couplings Mediated by SmI_2" J.Chem.Soc., Perkin Trans. 1 (in press). (1999)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1999-12-08  

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