Skip to main content
SpringerLink
Log in

Transformed steroids Communication 37. Effect of reaction medium on opening of 16α,17α-epoxy-16β-methyl-δ5-pregnen-3β-ol-20-one

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A study was made of the direction of opening 16α,17α-epoxy-16β-methyl-Δ5-pregnan-3β-ol-20-one as a function of the nature of the solvent and the catalyst.

  2. 2.

    In all cases it was found that only the C16-O bond of the oxide ring is cleaved, in which connection a mixture of the 16-methyl-δ15-17-hydroxy and 16-methylene-17-hydroxy steroids is formed.

  3. 3.

    It was established that a definite relationship exists between the composition of the formed mixture and the nature of the solvent, and a theory was expressed regarding the reasons for this relationship.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. A. A. Akhrem, A. V. Kamernitskii, and N. S. Pavlova-Grishina, this issue, p. 2414.

  2. A. A. Akhrem, V. A. Dubrovskii, A. V. Kamernitskii, and A. V. Skorova, Izv. Akad. Nauk SSSR, Ser. Khim., 2792 (1969).

  3. A. A. Akhrem, A. V. Kamernitskii, and A. V. Skorova, Izv. Akad. Nauk SSSR, Ser. Khim., 654 (1970).

  4. E. Batres, T. Cardenas, J. A. Edwards, G. Monroy, O. Mancera, C. Djerassi, and H. J. Ringold, J. Org. Chem.,26, 871 (1961).

    Google Scholar 

  5. G. I. Gregory, J. S. Hunt, P. J. May, F. A. Nice, and G. H. Phillipps, J. Chem. Soc., C, 2201 (1966).

    Google Scholar 

  6. K. Syhora, Collection Czech. Chem. Commun.,26, 107, 1034 (1961);29, 1163, 1173, 2513 (1964);30, 2771 (1965);31, 2768 (1966).

    Google Scholar 

  7. D. Taub, R. D. Hoffsommer, and N. L. Wendler, Chem. Ind. (London), 251 (1961); J. Org. Chem.,29, 3486 (1964).

  8. K. Syhora and R. Mazac, Collection Czech. Chem. Commun.,29, 2351 (1964).

    Google Scholar 

  9. T. L. Popper, J. N. Gardner, R. Neri, and H. L. Herzog, J. Med. Chem.,12, 393 (1969).

    Google Scholar 

Download references

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

Authors
  1. A. A. Akhrem
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Vesela
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Kamernitskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See [1] for Communication 36.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2552–2557, November, 1971.

The authors express their gratitude to V. A. Korenevskii for taking and deciphering the NMR spectra.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Akhrem, A.A., Vesela, I.V. & Kamernitskii, A.V. Transformed steroids Communication 37. Effect of reaction medium on opening of 16α,17α-epoxy-16β-methyl-δ5-pregnen-3β-ol-20-one. Russ Chem Bull 20, 2417–2421 (1971). https://doi.org/10.1007/BF00854325

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00854325

Keywords

Search

Navigation