The epoxidation of 3β-acetoxy-5α-cholesta-8,14-diene with 1 molar equiv of m-chloroperbenzoic acid has been found useful for the synthesis of 15-oxygenated sterols. The major product of the reaction, 3β-acetoxy-14α,15α-epoxy-5α-cholest-8-ene, is decomposed on silica to a (1:1) mixture of 3β-acetoxy-5α-cholesta-8(14),9-(11)-dien-15α-ol and 3β-acetoxy-5α-cholest-8(14)-ene-9α,15α-diol. The minor product obtained in the epoxidation is 3β-acetoxy-8α,9α-epoxy-5α-cholest-14-ene
15-Oxygenated sterols by m-chloroperbenzoic acid oxidation of 3β-acetoxy-5α-cholesta-8,14-diene / M. Anastasia, P. Allevi, A. Fiecchi, A. Scala. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 46:16(1981), pp. 3265-3267.
15-Oxygenated sterols by m-chloroperbenzoic acid oxidation of 3β-acetoxy-5α-cholesta-8,14-diene
M. AnastasiaPrimo
;P. AlleviSecondo
;
1981
Abstract
The epoxidation of 3β-acetoxy-5α-cholesta-8,14-diene with 1 molar equiv of m-chloroperbenzoic acid has been found useful for the synthesis of 15-oxygenated sterols. The major product of the reaction, 3β-acetoxy-14α,15α-epoxy-5α-cholest-8-ene, is decomposed on silica to a (1:1) mixture of 3β-acetoxy-5α-cholesta-8(14),9-(11)-dien-15α-ol and 3β-acetoxy-5α-cholest-8(14)-ene-9α,15α-diol. The minor product obtained in the epoxidation is 3β-acetoxy-8α,9α-epoxy-5α-cholest-14-ene
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