Steroidal analogues of unnatural configuration. Part IV. Stereoselective additions to the 5,6-bond of 4,4,14α-trimethyl-19(10 → 9β)abeo-10α-pregn-5-enes and correlation with the related 19-nor-10α-series

Abstract

The hindered 5,6-double bond of 4,4,14α-trimethyl-19(10 → 9β)abeo-10α-pregn-5-enes undergoes stereoselective cis-addition with peroxy-acid and osmium tetroxide to give 5β,6β-disubstituted products. A rigorous proof of the configurational assignments, by correlation with 5,6-disubstituted derivatives of 4,4,14α-trimethyl-19-nor-10α-pregn-5-enes, is presented.