Stereochemistry of some reactions of ring D of the diterpenoid aphidicolin
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- Vol. 23 (1) , 41-46
- https://doi.org/10.1039/p19920000041
Abstract
The stereochemistry of a number of reactions at C-16 in the diterpenoid, aphidicolin, has been examined, and, unlike simpler bicyclo[3.2.1]octane derivatives, there is only a limited degree of stereospecificity. The 15-enes can be prepared by dehydration of the epimeric 16-alcohols. Epoxidation and catalytic reduction have been shown to occur from the β-(exo)-face of the bicyclo[3.2.1]octene system that constitutes rings C and D of the aphidicol-15-enes. The stereochemistry or aphidicolane-3α,16α,18-triol has been established by X-ray crystallography.Keywords
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