Oxyfunctionalization of steroids by dioxiranes: Site and stereoselective C14 and C17 hydroxylation of pregnane and androstane steroids.

Abstract Dimethyldioxirane showed to be site and stereoselective in the CH oxygen insertion at C 14 and C 17 positions of pregnane and androstane steroids. Fine steric control and evidence for the influence of the carbonyl group on the dioxirane reactivity are reported.