The Prévost reaction with 5α-androst-2-ene

Abstract

Treatment of 5α-androst-2-ene with silver benzoate and iodine gives, as major products, the diaxial and diequatorial esters 5α-androstane-2β,3α-diol dibenzoate and 5α-androstane-2α,3β-diol dibenzoate, and the iodo-diester, 1 α-iodo-5α-androstane-2β,3β-diol dibenzoate. A mechanism for the Prévost reaction involving two regioisomeric iodo-benzoates has been established by the preparation and solvolysis of the intermediate iodo-benzoates.

The four epimeric 5α-androstane-2,3-diols have been prepared.