Chemistry of Natural Compounds

, Volume 21, Issue 5, pp 570–578 | Cite as

13C NMR spectra of biologically active compounds. II. 11-Deoxy-16- and 17-aryloxyprostaglandins

  • G. A. Tolstikov
  • L. M. Khalilov
  • A. A. Panasenko
  • M. A. Danilova
  • M. S. Miftakov


The13C NMR spectra of the initial ω-aryloxy chains and the final 16-and 17-aryloxyprostaglandins of the 11-deoxy series have been investigated, and stereochemical assignments have been made for the diastereomeric pairs. A weakening of the diastereotopic effects in the spectra of the 15- and 16-methyl-substituted 16- and 17-phenoxypropstaglandins to 0.1 ppm has been shown.


Carbon Atom Trans Isomer Chiral Center Butyl Ester Trimethylsiloxy 


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Literature cited

  1. 1.
    A. K. Banerjee, B. J. Broughton, T. S. Burton, et al., Prostaglandins,22, 167 (1982).CrossRefGoogle Scholar
  2. 2.
    G. A. Tolstikov, L. M. Khalikov, A. A. Panasenko, et al., Khim. Prir. Soedin., 314 (1985).Google Scholar
  3. 3.
    T. Pekhk, T. Vilimyae, and N. Samel, Izv. Akad. Nauk ESSR, Khim.,31, No. 2, 85 (1982).Google Scholar
  4. 4.
    G. C. Levy, R. L. Lichter, and G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance Spectroscopy, 2nd edn., Wiley-Interscience, New York (1980), p. 338.Google Scholar
  5. 5.
    G. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York (1972), p. 559.Google Scholar
  6. 6.
    E. Pretsh, T. Clerc, J. Siebel, and W. Simon, Tabellen zur Strukturaufklärung Organischer Verbindungen mit Spektroskopischen Methoden, Springer, New York (1966), p. 95.Google Scholar
  7. 7.
    A. A. Panasenko, L. M. Khalilov, I. M. Salimgareeva, and V. N. Yur'ev, Izv. Akad. Nauk SSSR, Ser. Khim., 938 (1979).Google Scholar
  8. 8.
    M. Christl, H. J. Reich, and J. D. Roberts, J. Am. Chem. Soc.,93, No. 14, 3463 (1971).CrossRefGoogle Scholar
  9. 9.
    G. A. Tolstikov, N. A. Danilova, and M. S. Miftakhov, in: Synthesis and Investigation of the Prostaglandins. Abstracts of Lectures of the Xth All-Union Conference [in Russian], Riga (1982), p. 54.Google Scholar
  10. 10.
    N. A. Danilova, G. A. Tolstikov, M. S. Miftakhov, M. I. Lopp, and Yu. E. Lille, Dokl. Akad. Nauk SSSR,273, No. 3, 620 (1983).Google Scholar

Copyright information

© Plenum Publishing Corporation 1986

Authors and Affiliations

  • G. A. Tolstikov
  • L. M. Khalilov
  • A. A. Panasenko
  • M. A. Danilova
  • M. S. Miftakov

There are no affiliations available

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