A synthetic approach to the tricyclic system of forskolin from D-galactose
โ 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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โฆ 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
๐ SIMILAR VOLUMES
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
An advanced bicyclic BC intermediate towards the total synthesis of verrucarol has been prepared from D-galactose via an intramolecular aldehyde-allylstannane reaction.