The chemistry of 9α-hydroxysteroids. 3. Methods for selective formation and dehydrations of 17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one

Article abstract of DOI:10.1016/0039-128X(90)90005-V

Two methods to produce the 17-cyanohydrin, using potassium cyanide in acetic acid/methanol or acetone cyanohydrin with aqueous sodium hydroxide, were followed with 9α-hydroxyandrost-4-ene-3,17-dione, both providing 17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one.The selectivity of one of these methods, that which uses acetone cyanohydrin, is not in agreement with a comparable reaction with the 9α-unsubstituted androst-4-ene-13,17-dione to give the 17α-cyano-17β-hydroxy product, as reported in the literature and confirmed by us.The 9α-hydroxy and 17α-hydroxy groups were used for the regioselective introduction of 9(11)- and 16(17)-double bonds by dehydrating 17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one under different conditions.