The Woodward-Prévost reaction with 5α-Androst-7-ene

Abstract

5α-Androst-7-ene (8) has been prepared from 3β-hydroxyandrost-5-en-17-one by a route which is superior to the usual procedure for making steroidal 7-enes. The products from reaction of 5α- androst-7-ene under Woodward-Prevost conditions are 5α -androsta-7,9(11)-diene (29),5α-androsta- 7,14-diene (30), 5α-androst-8-ene-7a,11β-diol diacetate (31) and 5α -androst-8-ene-7α,11α-diol diacetate (32). The isolation of 5α -androsta-7,9(11)-diene and its independent conversion into the diacetates (31) and (32) supports a mechanism proposed by Djerassi et al. for the analogous oxidation of 5α-cholest-7-ene (1).