Steroidal analogues of unnatural configuration. Part 13. Synthesis and ring B reactions of 4,4,9-trimethyl-9β,10α-estr-5-ene

Abstract

The conversion of 17β-hydroxy-9-methyl-9β,10α-estr-4-en-3-one into 4,4,9-trimethyl-9β,10α-estr-5-ene is described, and certain ring B transformations of the latter compound are compared and contrasted with those carried out upon 4,4,14α-trimethyl-19(10 → 9β)abeo-10α-pregn-5-en-11-one in an earlier study. The stereochemical implications of these results are discussed.