Microbiological hydroxylation of steroids. Part VI. Hydroxylation of simple mono- and di-oxygenated 5α-androstanes and of 3-oxoestranes with the fungus Aspergillus ochraceus

Of the eleven 5α-androstane monoketones, only two are hydroxylated by Aspergillus ochraceus. 5α-Androstan-3-one (and 5α-estran-3-one and the related Δ4-3-ketones) give 11α-hydroxy- and then 6β,11α-dihydroxy-compounds; 5α-androstan-17-one gives a 7β,11α-dihydroxy-derivative.The predilection of A. ochraceus for 11α-hydroxylation is emphasized by the results with dioxygenated andro-stanes which, although representing a range of structural types, are all hydroxylated efficiently at the 11α-position.