The application of dimethyldioxirane for the selective oxidation of polyfunctional steroids.
Oxidation and epoxidation reactions of a series of structurally different steroids related to methyl 5 beta-cholanoates having hydroxyl groups and/or double bonds by treatment with dimethyldioxirane (DMDO) are described. Steroidal alcohols, olefines, and unsaturated alcohols and conjugated enones with DMDO were transformed into ketones, epoxides, and epoxy-ketones, respectively, in good isolated yields. The regio- and stereoselectivities for DMDO reaction differing from those observed for organic peracids, tert-butyl hydroperoxide and alkaline hydrogen peroxide are also discussed.
Department of Chemistry, College of Humanities and Sciences, Nihon University, Setagaya, Sakurajousui, Tokyo 156-8550, Japan.
T
T
Sasaki
R
R
Nakamori
T
T
Yamaguchi
Y
Y
Kasuga
T
T
Iida
T
T
Nambara
D004852:Epoxy Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D013256:Steroids / Q000737:chemistry*
D004852:Epoxy Compounds; D013256:Steroids; C064455:dimethyldioxirane