Chemistry of Natural Compounds

, Volume 13, Issue 4, pp 439–443 | Cite as

Oxidative transformations of cembrane diterpenoids III. Epoxycembrenes

  • V. A. Raldugin
  • L. Ya. Korotkikh
  • A. I. Rezvukhin
  • V. A. Pentegova
Article
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Summary

1. It has been established that the epoxidation of cembrene with perbenzoic and peracetic acids takes place stereospecifically at each of the trisubstituted double bonds with the formation of 4S,5R-, 7S,8S-, and 11S,12S-monoepoxycembrenes, the structures and absolute configurations of which have been established by spectral methods.

2. Epoxidation of cembrene at the C11–C12 double bonds under the conditions used takes place preferentially as compared with epoxidation at the C7–C8 double bond.

Keywords

Epoxide Diol Benzoyl Chloride Peracetic Acid Asymmetric Center 
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Literature cited

  1. 1.
    A. J. Weinheimer, R. E. Middlebrook, J. O. Bledsoe, and W. E. Marsico, J. Chem. Soc., (D), 384 (1968).Google Scholar
  2. 2.
    M. B. Hossain and D. van der Helm, Rec. Trav. Chim.,88, 1413 (1969).CrossRefGoogle Scholar
  3. 3.
    J. P. Springer, J. Clardy, R. H. Cox, H. G. Gutler, and R. J. Cole, Tetrahedron Lett., 2737 (1975).Google Scholar
  4. 4.
    V. A. Raldugin, A. I. Rezvukhin, and V. A. Pentegova, Khim. Prirodn. Soedin., 598 (1971).Google Scholar
  5. 5.
    V. S. Joshi, N. P. Damodaran, and Sukh Dev., Tetrahedron,24, 5817 (1968).CrossRefGoogle Scholar
  6. 6.
    U. Nagai and H. Iga, Tetrahedron,26, 725 (1970).CrossRefGoogle Scholar
  7. 7.
    M. G. B. Drew, D. H. Templeton, and A. Zalkin, Acta Cryst.,25B, 261 (1969).CrossRefGoogle Scholar
  8. 8.
    V. A. Raldugin, V. K. Fedorov, and V. A. Penterova, Khim. Prirodn. Soedin., 391 (1976).Google Scholar
  9. 9.
    V. A. Raldugin, A. I. Rezvukhin, L. Ya. Korotkikh, and V. A. Pentegova, Khim. Prirodn. Soedin., 54 (1977).Google Scholar
  10. 10.
    F. J. Schmitz, D. J. Vanderah, and L. S. Ciereszko, J. Chem. Soc., D, 407 (1974).Google Scholar
  11. 11.
    G. Berti, F. Bottari, B. Macchia, and F. Macchia, Tetrahedron,21, 3277 (1965).CrossRefGoogle Scholar
  12. 12.
    F. P. Greenspan, J. Am. Chem. Soc.,68, 907 (1946).CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • V. A. Raldugin
  • L. Ya. Korotkikh
  • A. I. Rezvukhin
  • V. A. Pentegova

There are no affiliations available

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