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Transformed steroids

Communication 82. Hydroxylation of 3-acetates of ethyl esters of 21,24-dinor- and 24-norchola-5,16,20(22)-trien-3β-ol-23-oic acids

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Conclusions

  1. 1.

    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.

  2. 2.

    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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Literature cited

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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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    A. V. Kamernitskii, V. A. Krivoruchko, R. P. Litvinovskaya, and I. G. Reshetova, Izv. Akad. Nauk SSSR, Ser. Khim.,1975, 2073.

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    A. A. Akhrem, A. V. Kamernitskii, R. P. Litvinovskaya, and I. G. Reshetova, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 161.

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    B. M. Zoiotarev, A. V. Kamernitskii, V. A. Krivoruchko, R. P. Litvinovskaya, I. G. Reshetova, and O. S. Chizhcv, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 1061.

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Additional information

See [1] for Communication 81.

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

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Keywords

  • Ester
  • H2O2
  • Steroid
  • Ethyl
  • Epoxidation