Synthesis of 17α-Hydroxy Steroids: B-Norepitestosterone

Abstract

The key intermediate VI was prepared by two ways: by B ring contraction of an androst-5-ene-3β,17α-diol derivative I and by configurational inversion of the 17β-hydroxy group in a B-norandrost-5-ene-3β,17β-diol derivative XII. B-Norepitestosterone (IX) and its potentional metabolite X were then prepared by standard methodology. Both these compounds appear to be inhibitors of 5α-reductase.