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Transformed steroids

Communication 50. Stereochemical and structural direction of reaction of 16β,17β-epoxypregn-5-en-3β-ol-20-one and its 3-acetate with thiocyanic acid

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

Conclusions

  1. 1.

    The opening of 16β,17β-epoxyisopregn-5-en-3β-ol-20-one and its 3-acetate with thiocyanic acid proceeds preferentially by the trans-mechanism, with a cleavage of the C16-O and C17-O bonds.

  2. 2.

    The reaction for the cis-opening of the 16β,17β-oxide ring, with a cleavage of the Cβ-O bond, proceeds simultaneously, as a result of which isopregn-5-en-3β-ol-20-one-[16β,17β-d]-1′,3′-oxa-2′-thiolanone is formed.

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Literature cited

  1. A A Akhrem, A. V. Kamernitskii, I. G. Reshetova, and I. N. Voznesenskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 573 (1972).

  2. A. A. Akhrem, A. M. Turuta, and Z. I. Istomina, Izv. Akad. Nauk SSSR, Ser. Khim., 1354 (1972).

  3. P. Crabbe, Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry, San Francisco-London-Amsterdam (1965).

  4. A. A. Akhrem, G. A. Kogan, A. M. Turuta, I. S. Kovnatskaya, and Z. I. Istomina, Izv. Akad. Nauk SSSR, Ser. Khim., 2688 (1972).

  5. A. A. Akhrem, G. A. Kogan, A. M. Turuta, I. S. Kovnatskaya, and Z. I. Istomina, Izv. Akad. Nauk SSSR, Ser. Khim., 2100 (1971).

  6. J. C. Danilewicz and W. Klyne, J. Chem. Soc. C, 1306 (1965).

  7. N. N. Mel'nikov and N. D. Sukhareva, Reactions and Study Methods for Organic Compounds [in Russian], Vol. 8, Goskhimizdat (1959).

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Authors and Affiliations

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

    A. A. Akhrem, Z. I. Istomina, A. M. Turuta & G. A. Kogan

Authors
  1. A. A. Akhrem
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  2. Z. I. Istomina
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  3. A. M. Turuta
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  4. G. A. Kogan
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Additional information

See [1] for the preceding communication in this series.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 90–96, January, 1973.

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Akhrem, A.A., Istomina, Z.I., Turuta, A.M. et al. Transformed steroids. Russ Chem Bull 22, 82–87 (1973). https://doi.org/10.1007/BF00854120

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  • DOI: https://doi.org/10.1007/BF00854120

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