Microbiological hydroxylation of steroids. Part I. Proton magnetic resonance spectra of ketones, alcohols, and acetates in the androstane, pregnane, and œstrane series

Abstract

Structural investigation of the products obtained by microbiological hydroxylation of substrates in the androstane, pregnane, and œstrane series has involved examining the 1H n.m.r. spectra of 344 steroids, 243 of them being new compounds. Mild oxidation of the products gives polyketones in which the positions of the oxo-groups are characterised by the chemical and solvent shifts of the 18-H and 19-H signals. This information is supplemented by the chemical shifts of the products' 18-H and 19-H signals, and by the positions and form of their CH–OH resonances: the latter are especially useful in establishing the configurations of the hydroxy-groups.