Chemistry of Natural Compounds

, Volume 7, Issue 5, pp 582–585 | Cite as

α-,β-, andγ-pinacenes — new diterpenoids from the oleoresins of Pinus koraiensis and P. sibirica

  • V. A. Raldugin
  • N. K. Kashtanova
  • V. A. Pentegova


1. From the oleoresin ofPinus koraiensis Sieb. et Zucc we have isolated new diterpenoids — α-, β-, and γ-pinacenes — for which the structure of 7-trans, 11-trans-cembra-1,3,7,11-tetraene has been shown. They differ by the configurations of the double bonds of the conjugated diene system. α- and β-Pinacenes have also been isolated from the oleoresin ofPinus sibirica R. Mayr.

2. The isomerization of cembrene with iodine under conditions favoring an ionic reaction has led to α-, β-, and γ-pinacenes.


Geometrical Isomer Methine Proton Tetraene Vinyl Methyl Isopropyl Group 


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Literature cited

  1. 1.
    Y. Sebe, J. Chem. Soc. Japan,56, 1118 (1935).Google Scholar
  2. 2.
    N. K. Kashtanova, A. I. Lisina, and V. A. Pentegova, Khim. Prirodn. Soedin.,4, 52 (1968).Google Scholar
  3. 3.
    V. A. Raldugin, N. K. Kashtanova, and V. A. Pentegova, Khim. Prirodn. Soedin.,6, 481 (1970).Google Scholar
  4. 4.
    É. N. Shmidt, N. K. Kashtanova, and V. A. Pentegova, Khim. Prirodn. Soedin.,6, 694 (1970).Google Scholar
  5. 5.
    L. M. Jackman, Applications of NMR Spectroscopy in Organic Chemistry, Pergamon Press, London (1959), p. 60.Google Scholar
  6. 6.
    N. P. Damodaran and Sukh Dev, Tetrahedron Lett.,1965, 1977.Google Scholar
  7. 7.
    K. Morikawa and Y. Hirose, Tetrahedron Lett.,1969, 1799.Google Scholar
  8. 8.
    E. K. Gustorf and J. Lettich, Tetrahedron Lett.,1968, 4689.Google Scholar
  9. 9.
    S. J. Rhoads, J. K. Chattopadhyay, and E. E. Waali, J. Org. Chem.,35, 3352 (1970).CrossRefGoogle Scholar
  10. 10.
    V. A. Raldugin, A. I. Rezvukhin, and V. A. Pentegova, Khim. Prirodn. Soedin.,7, 598 (1971).Google Scholar
  11. 11.
    W. J. Muizebelt and R. J. F. Nivard, J. Chem. Soc., B,1968, 921.Google Scholar
  12. 12.
    V. L. Heasley and P. H. Chamberlain, J. Org. Chem.,35, 539 (1970).CrossRefGoogle Scholar
  13. 13.
    V. Gold and M. Whittaker, J. Chem. Soc.,1951, 1184.Google Scholar
  14. 14.
    R. A. Ogg, J. Amer. Chem. Soc.,56, 526 (1934).CrossRefGoogle Scholar
  15. 15.
    V. A. Pentegova and N. K. Kashtanova, Khim. Prirodn. Soedin.,1, 223 (1965).Google Scholar

Copyright information

© Consultants Bureau 1974

Authors and Affiliations

  • V. A. Raldugin
  • N. K. Kashtanova
  • V. A. Pentegova

There are no affiliations available

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