Journal of the Chemical Society. Perkin transactions I p. 1735 - 1740 (1992)
Update date:2022-08-04
Topics:
Medelovici, Marioara
Glotter, Erwin
Treatment of 3β- and 3α-hydroxy-(acetoxy-)cholest-4-en-6-one and of 6β- and 6α-hydroxy-(acetoxy-)cholest-4-en-3-one with MCPBA gives two types of product, depending on the initial site of the peroxy acid attack.Attack at the carbonyl group gives a Baeyer-Villiger rearrangement leading first to enol lactones and then by epoxidation of the latter to epoxy lactones.Alternatively, attack at the double bond gives epoxy ketones which can subsequently undergo a Baeyer-Villiger rearrangement leading to epoxy lactones.With one exception (3α-hydroxycholest-4-en-6-one), the Baeyer-Villiger oxidation of the enone is the dominant process.Epoxidation of the double bond is suppressed in the presence of an axial 3α- or 6β-acetoxy group.
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Doi:10.1007/BF00766456
(1992)Doi:10.1002/adsc.200600410
(2007)Doi:10.1016/S0960-894X(02)00322-0
(2002)Doi:10.1002/anie.201203198
(2012)Doi:10.1039/c39920001005
(1992)Doi:10.1021/jo00050a042
(1992)
