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Intramolecular enone-furan photocycloadditions: Studies toward the synthesis of ginkgolides A and B

✍ Scribed by Michael T. Crimmins; James B. Thomas

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 243 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)93837-7

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✦ Synopsis

The synthesis of a pentacyclic model 14 for ginkgolides A and B has been accomplished utilizing an intramolecular furan-enone photochemical cycloaddition as the key transformation. Ginkgolides A and B 1,2, hexacyclic trilactones obtained from extracts of the ancient tree Ginkgo Biloba, were isolated and characterized by Nakanishi in 1967.3 While these compounds are known antagonists of platelet activating factor (PAF) and have already found important medicinal applications in Europe and Asia,4 there has been relatively little effort directed toward their synthesis until recentiy.~-8 In 1988 Corey reported the first synthesis of ginkgolide B5 and a few other model studies have been disclosed.6-* We report here our studies on the synthesis of a pentacyclic analog of ginkgolides A and B which should serve as a model for further development of a new synthetic approach to these complex d&penes.

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