Chemistry of Natural Compounds

, Volume 10, Issue 4, pp 496–503 | Cite as

Absolute configuration of vinerine and vineridine

  • M. R. Yagudaev
  • V. M. Malikov
  • S. Yu. Yunusov
Article
  • 25 Downloads

Summary

On the basis of an analysis of the circular dichroism and NMR spectra the absolute configuration 7R, 3R, 4S, 15S, 19S, 20S has been established for vinerine; 7S, 3R, 4S, 15S, 19S, 20S for vineridine; and 7S, 3S, 4R, 15S, 19S, 20S for N-acetylvinerine.

Keywords

Circular Dichroism Lactam Nuclear Overhauser Effect Paramagnetic Shift Deuteropyridine 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    Sh. Z. Kasymov, P. Kh. Yuldashev, and S. Yu. Yunusov, Dokl. Akad. Nauk SSSR,162, 102 (1965).PubMedGoogle Scholar
  2. 2.
    Sh. Z. Kasymov, P. Kh. Yuldashev, and S. Yu. Yunusov, Dokl. Akad. Nauk SSSR,163, 1400 (1965).PubMedGoogle Scholar
  3. 3.
    Sh. Z. Kasymov, P. Kh. Yuldashev, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 260 (1966).Google Scholar
  4. 4.
    H. M. McConnell, J. Chem. Phys.,27, 226 (1957).CrossRefGoogle Scholar
  5. 5.
    A. D. Buckingham, Can. J. Chem.,38, 300 (1960).CrossRefGoogle Scholar
  6. 6.
    R. F. Zurcher, Progr. Nucl. Magn. Res. Spectroscopy,2, Ch. 5 (1967).Google Scholar
  7. 7.
    C. E. Johnson and F. A. Bovey, J. Chem. Phys.,29, 1012 (1958).CrossRefGoogle Scholar
  8. 8.
    B. Pullman and A. Pullman, Quantum Biochemistry, Wiley, New York (1965).Google Scholar
  9. 9.
    S. McLean, K. Palmer, and L. Marion, Can. J. Chem.,38, 1547 (1963).CrossRefGoogle Scholar
  10. 10.
    A. M. Monro and M. J. Sewel, Tetrahedron Lett., 595 (1969).Google Scholar
  11. 11.
    J. B. Hendrickson and J. J. Sims, Tetrahedron Lett., 929 (1963).Google Scholar
  12. 12.
    A. H. Beckett, C. M. Lee, and A. W. Tackel, Tetrahedron Lett., 1709 (1963).Google Scholar
  13. 13.
    W. F. Trager et al. Tetrahedron,24, 523 (1968).CrossRefGoogle Scholar
  14. 14.
    M. Zanger, W. W. Simons, and A. R. Gennaro, J. Org. Chem.,33, No. 9, 3673 (1968).CrossRefGoogle Scholar
  15. 15.
    K. Nagarajan, M. D. Nair, and P. M. Pillai, Tetrahedron,23, 1683 (1967).CrossRefGoogle Scholar
  16. 16.
    G. Fraenkele et al., J. Am. Chem. Soc.,82, 5846 (1960).CrossRefGoogle Scholar
  17. 17.
    H. Spiesecke and W. G. Shneider, Tetrahedron Lett., 468 (1961).Google Scholar
  18. 18.
    R. A. Bell and J. K. Saunders, Can. J. Chem.,48, 1114 (1970).CrossRefGoogle Scholar
  19. 19.
    N. Finch et al., J. Am. Chem. Soc.,84, 3871 (1962).CrossRefGoogle Scholar
  20. 20.
    A. F. Beecham et al., Austr. J. Chem.,21, 491 (1968).CrossRefGoogle Scholar
  21. 21.
    J. L. Pousset, J. Poulsson, R. J. Shine, and M. Shamma, Bull. Soc. Chim. Fr.,8, 2766 (1967).PubMedGoogle Scholar
  22. 22.
    C. Pascard-Billy, Bull. Soc. Chim. Fr.,8, 3289 (1968).PubMedGoogle Scholar
  23. 23.
    J. L. Pousset, J. Polsson, and F. Legrand, Tetrahedron Lett., 6283 (1966).Google Scholar
  24. 24.
    J. L. Pousset, J. Polsson, Tetrahedron Lett., 1919 (1967).Google Scholar
  25. 25.
    M. Shamma et al., J. Amer. Chem. Soc.,89, 1739 (1967).CrossRefGoogle Scholar
  26. 26.
    E. Wenkert and N. V. Bringi, J. Amer. Chem. Soc.,81, 1474 (1959).CrossRefGoogle Scholar
  27. 27.
    M. Shamma and J. M. Richey, J. Amer. Chem. Soc.,85, 2507 (1963).CrossRefGoogle Scholar
  28. 28.
    G. B. Yeoh et al., Tetrahedron Lett., 931 (1966).Google Scholar
  29. 29.
    E. Wenkert et al ., Tetrahedron Lett., 822 (1961).Google Scholar
  30. 30.
    K. C. Chan, Tetrahedron Lett., 931 (1966).Google Scholar
  31. 31.
    Yu. Yu. Samitov, Dokl. Akad. Nauk SSSR,164, 347 (1965).Google Scholar
  32. 32.
    R. S. Cahn and C. K. Ingold, J. Chem. Soc., 612 (1951).Google Scholar
  33. 33.
    R. S. Cahn, C. K. Ingold, and V. Prelog, Angew. Chem.,5, 385 (1966).CrossRefGoogle Scholar
  34. 34.
    J. W. ApSimon et al., Tetrahedron,23, 2339 (1967).CrossRefGoogle Scholar

Copyright information

© Plemum Publishing Corporation 1976

Authors and Affiliations

  • M. R. Yagudaev
  • V. M. Malikov
  • S. Yu. Yunusov

There are no affiliations available

Personalised recommendations