Studies in the steroid group. Part LXXXIV. Preparation and reactions of 15-oxygenated androstanes

Abstract

Treatment of 15β, 16β-epoxy-5α-androstan-17-one with hydrazine and toluene-p-sulphonic acid in air gives 5α-androstan-15β-ol; this step markedly improves the chemical route to 5α-androstan-15-one from the 3-ketone. The 15-ketone is also readily obtained from 12β,15α-dihydroxy-5α-androstan-3-one (prepared by microbiological hydroxylation of 5α-androstan-3-one).Two series of substituted (mainly oxygenated) androstanes are described : those substituted at position 15 or at positions 15 and 17, and those substituted at the 12- and 15-, or at the 3-, 12-, and 15-positions.