Skip to main content
Log in

Transformed steroids 126. Synthesis and stereochemistry of isomeric androsta-D'-pentaranes (15,16-cyclohex-3′-enoandrostanes)

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

Conclusions

Condensation of androsta-5,16-diene-17-one with 1,3-dienes at high pressure proceeds nonselectively, and leads to two diastereomeric cycloadducts, while in the presence of anhydrous AlCl3 15Β,16Β-cycloadduct is formed stereospecifically.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. A. A. Akhrem, L. E. Kulikova, I. S. Levina, and Yu. A. Titov, Izv. Akad. Nauk SSSR, Ser. Khim., 1358 (1972).

  2. A. A. Akhrem, A. V. Kamernitskii, L. E. Kulikova, and I. S. Levina, Izv. Akad. Nauk SSSR, Ser. Khim., 444 (1978).

  3. A. V. Kamernitskii, L. E. Kulikova, and I. S. Levina, Izv. Akad. Nauk SSSR, Ser. Khim., 1395 (1978).

  4. A. A. Akhrem, I. V. Sotskova, L. E. Kulikova, A. I. Terekhina, I. S. Levina, Yu. A. Titov, O. M. Kulyabko, and F. A. Rudzum, Dokl. Akad. Nauk SSSR,209, 504 (1973).

    Google Scholar 

  5. A. V. Kamernitskii, L. E. Kulikova, I. S. Levina, V. V. Korkhov, and G. V. Nikitina, Khim. Farm. Zh., No. 9, 72 (1980).

    Google Scholar 

  6. R. W. Kelly and P. I. Sykes, J. Chem. Soc. C, 416 (1968).

    Google Scholar 

  7. A. V. Kamernitskii, V. N. Ignatov, I. S. Levina, and B. S. él'yanov, Izv-Akad. Nauk SSSR, Ser. Khim., 1902 (1980).

  8. A. S. Onishchenko, The Diene Synthesis [in Russian], Izd. Akad. Nauk SSSR, Moscow (1963).

    Google Scholar 

  9. K. M. Wellman and C. Djerassi, J. Am. Chem. Soc.,87, 60 (1965).

    Google Scholar 

  10. A. D. Cross and C. Beard, J. Am. Chem. Soc.,86, 5317 (1964).

    Google Scholar 

  11. E. W. Cantrall, R. Littel, S. Bernstein, J. Org. Chem.,29, 64 (1964).

    Google Scholar 

  12. U. Mende, B. Radüchel, W. Skuballa, and H. Vorbrüggen, Tetrahedron Lett. 629 (1975).

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2147–2151, September, 1982.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kamernitskii, A.V., Galakhova, T.N., Levina, I.S. et al. Transformed steroids 126. Synthesis and stereochemistry of isomeric androsta-D'-pentaranes (15,16-cyclohex-3′-enoandrostanes). Russ Chem Bull 31, 1896–1900 (1982). https://doi.org/10.1007/BF00952397

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00952397

Keywords

Navigation