The microbiological hydroxylation of 3, 16-disubstituted androstanes by Cephalosporium aphidicola

<p>5?-Androstane-3, 16-dione has been prepared by hydroboration and oxidation of 3?-hydroxy-5?-androst-16-ene. Reduction with sodium borohydride gave the 3?, 16?-diol. The fungus Cephalosporium aphidicola has been shown to hydroxylate 5?-androstane-3, 16-dione predominantly at the C-6? position with minor hydroxylation occurring at the C-7? and C-14? positions. In contrast hydroxylation of the 3?, 16?-diol took place at C-11?. The 3?-hydroxy-16?, 17?-epoxide was hydroxylated at the C-6? position.</p>