Aromatization of some steroidal enediols

Abstract

17β-Acetoxy-4β,5α-dihydroxyandrost-2-ene, 5α, 6α- and 5α,6β-dihydroxyandrost-2-en-17-one, 4β-acetoxy-3β-hydroxyandrost-5-en-17-one, and 3β,6β,17β-triacetoxyandrost-4-ene rearrange in hydrogen bromide–glacial acetic acid to form 4-methylestratrienes. Similar treatment of 6β,17β-diacetoxy-3β-hydroxyandrost-4-ene gives both 17β-acetoxy-4-methylestra-1,3,5(10)-triene and testosterone acetate. 3β,17β-Diacetoxy-6β-hydroxy-androst-4-ene gives 17β-acetoxyandrost-4-en-6-one.