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Transformed steroids

Communication 40. Wagner-meerwein rearrangement of 16α, 17α-epoxy-16β-methyl-δ5-pregnene-3β, 20/gb-diol

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The reduction of the acetate of 16α, 17α-epoxy-16β-methyl-Δ5-pregnen-3β-ol-20-one with sodium borohydride in tetrahydrofuran proceeds stereoselectively and apparently leads to only the 20β-isomer.

  2. 2.

    The opening of the oxide ring of 16α, 17α-epoxy-16β-methyl-Δ5-pregnene-3β, 20β-diol under the influence of perchloric acid proceeds mainly via the Wagner-Meerwein rearrangement and gives 16β, 17β-dimethyl-Δ5,13-18-norisopregnadiene-3β, 16α, 20β-triol, the structure of which was proved by counter synthesis.

  3. 3.

    The Grignard reaction with the diacetate of 17β-methyl-Δ5,13-18-norisopregnadiene-3β, 20β-diol-16-one proceeds to a large degree via attack from the front (from theβ-region).

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Literature cited

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Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    A. A. Akhrem, I. V. Vesela, A. V. Kamernitskii & E. P. Prokof'ev

Authors
  1. A. A. Akhrem
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  2. I. V. Vesela
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  3. A. V. Kamernitskii
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  4. E. P. Prokof'ev
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Additional information

See [1] for Communication 39.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1119–1123, May, 1972.

The present study was carried out in part in the Institute of Pharmacy and Biochemistry (Prague, Czechoslovakia), and the authors express their deep gratitude to the management and co-workers.

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Akhrem, A.A., Vesela, I.V., Kamernitskii, A.V. et al. Transformed steroids. Russ Chem Bull 21, 1071–1075 (1972). https://doi.org/10.1007/BF00853771

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  • DOI: https://doi.org/10.1007/BF00853771

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