Some observations on the preparation of 2-hydroxy-steroid 4-En-3-ones

Abstract

Improved experimental conditions are described for the preparation of 2β, 17β- and 2α,17β-dihydroxyestr-4-en-3-one diacetates and 2β-acetoxyandrost-4-ene-3,17-dione. 6β-Acetoxyandrost-4-ene-3,17-dione has been obtained, together with the 2-acetoxy-derivatives, by acetolysis of 6β-bromoandrost-4-ene-3,17-dione. N.m.r. and c.d. data for the 2-hydroxy-compounds and their acetates are interpreted in terms of alternative conformations for ring A.