Microbiological hydroxylation. Part XIII. Cyclododecanone and cyclopentadecanone as substrates for steroid-hydroxylating fungi

Abstract

Cyclododecanone and cyclopentadecanone are both hydroxylated in cultures of four steroid-hydroxylating fungi, but remarkably, neither is affected by Aspergillus ochraceus. Substitution is less selective and formation of only one or two major products is much less the rule than with steroid substrates; di- and poly-hydroxylation apparently proceed very rapidly. Initial attack occurs at the most remote carbon atoms, at C(8) with the C₁₅ ketone and at C(6)[and C(7)] with the C₁₂ ketone.