Together with the cis-hydroxylation of the Δ16-bond, the hydroxylation of the 3-acetates of the ethyl esters of 24-nor- and 21,24-dinorchola-5,16,20(22)-trien-3β-ol-23-oic acids with aqueous KMnO4 inpyridine gives the 3,16α, 22-triol 17,20-epoxides and their acetates.
The hydroxylation of the 21,24-dinor analogs with 30% H2O2 solution in the presence of OsO4 leads to a complex mixture of profoundly oxidized reaction products that are identified with difficulty. Only saponification of the carbethoxyl grouping occurs when alkaline H2O2 solution is used for the epoxidation.
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N. E. Voishvillo, A. V. Kamernitskii, A. Ya. Khaikova, I. G. Leont'ev, V. N. Paukov, and L. A. Nakhapetyan, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 1357.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1360–1364, June, 1976.
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Akhrem, A.A., Kamernitskii, A.V., Krivoruchko, V.A. et al. Transformed steroids. Russ Chem Bull 25, 1306–1309 (1976). https://doi.org/10.1007/BF00928077