Advertisement

Chemistry of Natural Compounds

, Volume 7, Issue 5, pp 577–581 | Cite as

The stereochemistry of cembrene and related diterpenoids

  • V. A. Raldugin
  • A. I. Rezvukhin
  • V. A. Pentegova
Article
  • 35 Downloads

Summary

1. It has been shown that the nonconjugated trisubstituted double bonds of cembrene, isocembrene, neocembrene, and isocembrol have the trans configuration, and the conjugated trisubstituted double bond of cembrene possesses the cis configuration.

2. The asymmetric center of neocembrene has the R configuration.

3. The stereochemistry of the product of the addition of hydrogen to cembrene and isocembrene on Pd and Ni catalysts is apparently determined solely by the conformation of the conjugated diene system in these diterpenoids.

Keywords

Maleic Anhydride Nuclear Overhauser Effect Trans Configuration Raney Nickel Asymmetric Center 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    A. J. Haagen-Smit, T. H. Wang, and N. T. Mirov, J. Amer. Pharm. Assoc., Sci. Ed.,40, 557 (1951).CrossRefGoogle Scholar
  2. 2.
    N. K. Kashtanova, A. I. Lisina, and V. A. Pentegova, Khim. Prirodn. Soedin.,4, 52 (1968).Google Scholar
  3. 3.
    É. N. Shmidt, N. K. Kashtanova, and V. A. Pentegova, Khim. Prirodn. Soedin.,6, 694 (1970).Google Scholar
  4. 4.
    W. G. Dauben, E. Thiessen, and P. R. Resnick, J. Org. Chem.,30, 1693 (1965).CrossRefGoogle Scholar
  5. 5.
    H. Kobayashi and S. Akiyoshi, Bull. Chem. Soc. Japan,36, 823 (1963).CrossRefGoogle Scholar
  6. 6.
    B. Kimland and T. Norin, Acta Chem. Scand.,22, 943 (1968).CrossRefGoogle Scholar
  7. 7.
    F. A. L. Anet and A. J. R. Bourn, J. Amer. Chem. Soc.,87, 5250 (1965).CrossRefGoogle Scholar
  8. 8.
    L. M. Jackman, Applications of NMR Spectroscopy in Organic Chemistry, Pergamon Press, London (1959), p. 60.Google Scholar
  9. 9.
    A. J. Bates, Z. K. Leszczynski, J. J. Phillipson, P. B. Wells, and G. R. Wilson, J. Chem. Soc., A, 2435 (1970).Google Scholar
  10. 10.
    R. H. Bates and D. M. Gale, J. Amer. Chem. Soc.,82, 5749 (1960).CrossRefGoogle Scholar
  11. 11.
    R. L. Augustine, Catalytic Hydrogenation, Marcell Dekker, New York (1965), p. 69.Google Scholar
  12. 12.
    J. B. Bream, D. C. Eaton, and H. B. Henbest, J. Chem. Soc., (1957), p. 1974.Google Scholar

Copyright information

© Consultants Bureau 1974

Authors and Affiliations

  • V. A. Raldugin
  • A. I. Rezvukhin
  • V. A. Pentegova

There are no affiliations available

Personalised recommendations