SYNTHESIS OF 5α-ANDROSTANE-3α,16α,17β-TRIOL FROM 3β-HYDROXY-5-ANDROSTEN-17-ONE

Article abstract of DOI:10.1016/0039-128X(84)90018-7

5α-Androstane-3α,16α,17β-triol was synthesized from 3β-hydroxy-5-androsten-17-one.The procedure involved catalytic hydrogenation of 3β-hydroxy-5-androsten-17-one to 3β-hydroxy-5α-androstan-17-one.This was followed by conversion of the 3β-hydroxy group to 3α-benzoyloxy group by the Mitsunobu reaction.Further treatment with isopropenyl acetate yielded 5α-androsten-16-ene-3α,17-diol 3-benzoate 17-acetate.This was then converted to 3α,17-dihydroxy-5α-androstan-16-one 3-benzoate 17-acetate via the unstable epoxide intermediate after treatment with m-chloroperoxybenzoic acid.LiAlH4 reduction of this compound formed 5α-androstane-3α,16α,17β-triol. 1H and 13C NMR of various steroids are presented to confirm the structure of this compound.