A Concise Synthesis of Ginkgolide M, a Minor Component of a Terpene Trilactone Fraction from Ginkgo biloba Roots

Sergei Bolshakov, Sergei V. Dzyuba,* John Decatur, and Koji Nakanishi*
Department of Chemistry, Columbia University, 3000 Broadway, New York, New York 10027
J. Nat. Prod., 2006, 69 (3), pp 429–431
DOI: 10.1021/np050403i
Publication Date (Web): February 22, 2006
Copyright © 2006 American Chemical Society and American Society of Pharmacognosy

 Dedicated to Dr. Norman R. Farnsworth of the University of Illinois at Chicago for his pioneering work on bioactive natural products.

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*

 To whom correspondence should be addressed. (S.V.D.) Tel:  +1 212 854 5356. Fax:  +1 212 932 1289. E-mail:  svd2102@columbia.edu. (K.N.) Tel:  +1 212 854 2169. Fax:  +1 212 932 1289. E-mail:  kn5@columbia.edu.

Abstract

Abstract Image

Ginkgolide M (GM), which is found only in the roots of the Ginkgo biloba tree and is an inhibitor of ligand-operated ion channels in the central nervous system, has been prepared in three steps from 10-benzylginkgolide C, an intermediate generated during the isolation and separation of ginkgolides from Ginkgo biloba leaf extract. The described synthetic sequence can be applied to access GM derivatives for biological studies.

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History

  • Published In Issue March 24, 2006
  • Received October 14, 2005

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