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1998 Fiscal Year Final Research Report Summary

Synthetic Studies on Protein Phosphatase Inhibitor Dysidiolide

Research Project

Project/Area Number 09672165
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

YAMADA Yasuji  Tokyo University of Pharmacy and Life Science, School of Pharmacy, Professor, 薬学部, 教授 (10057317)

Project Period (FY) 1997 – 1998
Keywordsdysidiolide / synthesis / Diels-Alder reaction / protein phosphatase cdc25A / protein phosphatase inhibitor / sponge / lipase
Research Abstract

Dysidiolide, a novel sesterterpenoid isolated from the Caribbean sponge Dysidia eiheria de Laubenfels, exhibits inhibition of the protein phosphatase cdc25A.Dysidiolide possesses a unique carbon skeleton with structural features that find no precedent in nature. Thus, its unique structure and biological activity prompted me to undertake the synthetic studies of dysidiolide. I have achieved following three heading in this study.
1. Exploitation of Synthetic Method for Decalin Part of Dysidiolide using Intramolecura Diels-Alder Reaction
I developed synthetic method for decalin part of dysidiolide using model compound. This synthesis involves preparation of alpha, beta-unsaturated lactone by intramolecura Diels-Alder reaction, stereoselective methylation by Me_2CuLi at C-6 position and stereoselective alkylation at C-7 position.
2. Formal Synthesis of (*)-Dysidiolide
Decalin part of dysidiolide was synthesized according to above method. Deoxyganation of the C-12 and C-24 positions and extension of side chain completed the formal synthesis of (*)-dysidiolide.
3. Synthesis of Optically Active Cyclohexene Derivative Using Lipase
Optically active cyclohexene derivative was synthesized by optical resolution using Lipase AK.This compound is useful for the synthesis of optically active dysidiolide as a starting material.
The synthesis of optically active dysidiolide is now in progress.

  • Research Products

    (2 results)

All Other

All Publications (2 results)

  • [Publications] Hiroaki Miyaoka, Yasuhiro Kajiwara, Miho Hara, Akira Suma and Yasuji Yamada: "Kinetic Resolution of Primary Alcohol attached Quaternary Carbon by Lipase-Catalyzed Acetylation" (in preparation).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hiroaki Miyaoka, Yasuhiro Kajiwara and Yasuji Yamada: "Total Synthesis of *-Dysidiolide" (in preparation).

    • 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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