The application of dimethyldioxirane for the selective oxidation of polyfunctional steroids |
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| Authors: | Sasaki T Nakamori R Yamaguchi T Kasuga Y Iida T Nambara T |
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| Institution: | Department of Chemistry, College of Humanities and Sciences, Nihon University, Setagaya, Sakurajousui, Tokyo 156-8550, Japan. |
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| Abstract: | 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. |
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