Microbiological hydroxylation. Part XIX. The action of an ant fungus (‘Acromyrmex fungus’) on oxygenated androstanes, pregnanes, and cholestanes

Abstract

The title fungus readily metabolises oxygenated derivatives of androstane and pregnane, but not cholestane. With the androstanes and pregnanes three basic processes occur: hydroxylation at positions determined by the directing influences of the substrates' oxygenated groups, Baeyer–Villiger type oxidation of 3- and 20-ketones (the latter corresponding to side-chain degradation of the pregnanes), and dehydrogenation(s) in ring A. With the exception, of substrates which direct hydroxylation to the 17-(or 16-) position, the processes all occur at comparable rates; and in general complex mixtures are formed from most substrates.