83603-61-6Relevant articles and documents
Microbial hydroxylation of steroids. 10. Rearrangement during epoxidation and hydroxylation, and the stepwise nature of these enzymic reactions
Holland, Herbert L.,Riemland, Elly
, p. 1121 - 1126 (2007/10/02)
A series of unsaturated steroids has been incubated with fungi which are known to hydroxylate at a site corresponding to the allylic position in the analogous saturated steroids.In some cases, the anticipated hydroxylation occurred without rearrangement of the double bond.In a number of instances, however, products were obtained whose structures implied that allylic rearrangement had occurred during the reaction.The formation of these products is consistent with a stepwise mechanism of enzymatic oxidation.Possible routes for product formation are presented which incorporate this proposal.