The application of dimethyldioxirane for the selective oxidation of polyfunctional steroids

Oxidation and epoxidation reactions of a series of structurally different s teroids related to methyl 5 beta -cholanoates having hydroxyl groups and/or double bonds by treatment with dimethyldioxirane (DMDO) are described. Ste roidal alcohols, olefines, and unsaturated alcohols and conjugated enones w ith DMDO were transformed into ketones, epoxides, and epoxy-ketones, respec tively, in good isolated yields. The regio- and stereoselectivities for DMD O reaction differing from those observed for organic peracids, tert-butyl h ydroperoxide and alkaline hydrogen peroxide are also discussed. (C) 2001 El sevier Science Ireland Ltd. All rights reserved.