15-Oxygenated Sterols by m-Chloroperbenzoic Acid Oxidation of 3β-Acetoxy-5α-cholesta-8,14-diene

DOI: 10.1021/jo00329a025

Source and publish data:

Journal of Organic Chemistry p. 3265 - 3267 (1981)

Update date:2022-08-05

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Authors:

Anastasia, Mario

Allevi, Pietro

Fiecchi, Alberto

Scala, Antonio

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Article abstract of DOI:10.1021/jo00329a025

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.

Full text of DOI:10.1021/jo00329a025

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