Skip to main content
Log in

High-resolution13C NMR spectra and structure of steroids of the pregnane series containing additional four-or six-membered rings D' at positions 16,17

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

Conclusions

  1. 1.

    An analysis was made of the high-resolution13C NMR spectra of nine new 20-ketoteroids modified in ring D with an additional cyclobutane, cyclobutene, cyclohexane, or cyclohexene ring D' at positions 16,17.

  2. 2.

    On the basis of the NOE coefficients the orientations of rings D' in relation to the steroid skeleton were determined. In the case of the cyclobutene ring D' it was shown that δC14 and δC12 are characteristic of the α,α and β,β orientations of ring D'.

  3. 3.

    During analysis of the mutual effects of ring D' and the steroid skeleton on their δ13C values an abnormally large descreening effect was found from the cyclobutene ring in the β,β orientation on δC14.

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. V. S. Bogdanov, E. G. Cherepanova, T. N. Galakhova, I. S. Levina, and A. V. Kamernitskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1038 (1984).

  2. M. I. Struchkova, A. Kh. Margaryan, and E. P. Serebryakov, Izv. Akad. Nauk SSSR, Ser. Khim., 57 (1980).

  3. A. V. Kamernitskii, V. N. Ignatov, I. S. Levina, V. S. Bogdanov, and E. G. Cherepanova, Izv. Akad. Nauk SSSR, Ser. Khim., 2397 (1985).

  4. J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York-London (1972), pp. 81, 84.

    Google Scholar 

  5. J. W. Blunt and J. B. Stothers, Org. Magn. Reson.,9, 441, 460 (1977).

    Google Scholar 

  6. W. L. Duax and D. A. Norton, Atlas of Steroid Structure, Vol. 1, Plenum Press, New York-London (1975), p. 572.

    Google Scholar 

  7. Z. I. Khazheeva, V. I. Simonov, A. V. Kamernitskii, L. E. Kulikova, V. N. Ignatov, and I. S. Levina, Kristallografiya,27, 697 (1982).

    Google Scholar 

  8. V. M. Tseikinskii, V. B. Rybakov, V. I. Simonov, A. V. Kamernitskii, V. N. Ignatov, and I. S. Levina, Bioorg. Khim.,6, 1872 (1980).

    Google Scholar 

  9. V. M. Tseikinskii, V. B. Rybakov, V. I. Simonov, A. V. Kamernitskii, L. E. Kulikova, and I. S. Levina, Bioorg. Khim.,6, 259 (1980).

    Google Scholar 

  10. Z. I. Khazheeva, A. V. Kamernitskii, L. E. Kulikova, I. S. Levina, and V. I. Simonov, Kristallografiya,26, 996 (1981).

    Google Scholar 

  11. J. B. Lambert and A. R. Wagenas, Org. Magn. Reson.,17, 265, 270 (1981).

    Google Scholar 

  12. L. Kohout, A. Kasal, V. Sanda, and H. Velgova, Collect Czech. Chem. Commun.,48, 173 (1983).

    Google Scholar 

  13. H. Günther, NMR Spectroscopy: An Introduction, Wiley (1980).

  14. E. L. Eliel and K. M. Pietrsiewics, Org. Magn. Reson.,13, 193 (1980).

    Google Scholar 

  15. G. W. Buchanan, S. H. Preusser, and V. L. Webb, Can. J. Chem.,62, 1308 (1984).

    Google Scholar 

  16. A. E. Kapul'skii, T. A. Shibanova, V. I. Simonov, L. E. Kulikova, I. S. Levina, and A. V. Kamernitskii, Bioorg. Khim.,11, 979 (1985).

    Google Scholar 

  17. G. Eagner and K. Wüthrich, J. Magn. Reson.,33, 675 (1979).

    Google Scholar 

  18. V. S. Bodganov, E. G. Cherepanova, I. G. Reshetova, I. G. Levi, and A. V. Kamernitskii, Izv. Akad. Nauk SSSR, Ser. Khim., 549 (1983).

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2315–2321, October, 1986.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bogdanov, V.S., Cherepanova, E.G., Levina, I.S. et al. High-resolution13C NMR spectra and structure of steroids of the pregnane series containing additional four-or six-membered rings D' at positions 16,17. Russ Chem Bull 35, 2119–2124 (1986). https://doi.org/10.1007/BF00957537

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00957537

Keywords

Navigation