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An angular hydroxylation route to taxanes: Facile access to the bridged AB ring system of taxol

✍ Scribed by Brahim Kerkar; Duc Do Khac; Marcel Fétizon; Frédéric Guir

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
145 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The 5-mesyloxy-12-alcohol lib, obtained in eight steps from 5a , via angular hydroxylation is transformed by Grob fragmentation into the highly functionalized taxane precursor 12.

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The Cyclopropylalkylidenecyclopropane Thermal Double Ring Expansion. A Novel Route to the Bicyclo[5.3.1]undecane Skeleton of the AB Ring System of Taxanes. -The mechanism of the reaction is explained by the initial formation of a diradical followed by opening to a homoallylic biradical which closes