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A synthetic approach to the tricyclic system of forskolin from D-galactose

โœ Scribed by Issam Hanna; Jean-Yves Lallemand; Philippe Wlodyka


Book ID
104214686
Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
319 KB
Volume
35
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The syntksis of tk mkydic system offorskolin by an intramolecular DieleAidcr reaction is described, smrdng from tnQ9-acetyl-D-gakactai.

Forskolln. a highly oxygenated labdane diterpcne, exhibits a broad range of physiological activities through its ability to activate adenylate cyclase. The therapeutic potential of this natural product combined with its highly challenging structure have 8erved to stimulate an impomurt synthetic activity in a munbu of laboratories.l2

In the major@ of the previous synthetic appmachcs, an lnnan~lecular Diels-Akler reaction wa8 selected a8 the key step for the construction of an adequately functionalized AB ring system. In almost all cases, the elaboration of ring C was carried out in the final stage8 of the synthesis. In a new synthetic approach, we


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ChemInform Abstract: A New Synthetic App
โœ I. HANNA; P. WLODYKA ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 37 KB ๐Ÿ‘ 2 views

The functionalized tricyclic framework (XI) of the diterpene forskolin is synthesized by an intramolecular Diels-Alder reaction of the dienyne (VII), which is obtained by stereoselective introduction of the C side chains at C-1 and C-2 of tri-O-acetyl-D-galactal (I) via C-Ferrier and Claisen-Ireland