18-Norandrosta-8,11,13-trienes. Part I. 11-Hydroxy-derivatives

Abstract

Formic acid rearrangement of 3β-acetoxy-17β-hydroxy-17α-methyl-5α-androst-8-en-11-one (1) and of 9α-bromo-17β-hydroxy-17α-methylandrost-4-ene-3,11 -dione (3) gave 3β-acetoxy-11 -hydroxy-17,17-dimethyl-18-nor-5α-androsta-8,11,13-triene (4) and 11 -hydroxy-17,17-dimethyl-18-norandrosta-4,8,11,13-tetraen-3-one (5) respectively. A similar attempt to form the corresponding 12-phenol from 3β-acetoxy-17β-hydroxy-17α-methyl-5α-androst-9(11)-en-12-one (13) resulted in the formation of 3β-acetoxy-17-methyl-5α-androsta-9(11),16-dien-12-one (14).