A convenient synthesis of 1α- and 1β-hydroxycholesterol |
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| Authors: | M.Lj. Mihailović Lj. Lorenc V. Pavlović J. Kalvoda |
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| Affiliation: | Department of Chemistry, Faculty of Science, University of Belgrade, and Institute of Chemistry, echnology and Metallurgy, Belgrade, Yugoslavia;Research Department, Pharmaceuticals Division, Ciba-Geigy Limited, Basle, Switzerland |
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| Abstract: | An efficient procedure for the preparation of 1α-hydroxycholesterol 3-acetate 4 is described, which starts from cholesterol and involves as key steps transannular cyclization of the ten-membered ring ontaining (E)-3β-acetoxy-5,10-seco-1(10)-cholesten-5-one 1 to the oxetane derivative 1α,5-epoxy-5α-cholestan-3β-ol acetate 3, and opening of the four-membered ether ring in the latter compound. 1β-Hydroxycholesterol diacetate 9 was obtained by oxidation of 4 to the 1-oxo derivative 8, followed by metal hydride reduction and acetylation. |
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| Keywords: | Address for correspondence: Deparment of Chemistry Faculty of Science Studentski trg 16 P.O. Box 550 11001 Belgrade Yugoslavia. |
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