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Chemistry of Natural Compounds

, Volume 24, Issue 2, pp 171–178 | Cite as

Cyclization and rearrangement of diterpenoids. VI. Products of dehydration of (1R,2S,7S,10S,12S,13S)-2,6,6,10,12-pentamethyltetracyclo[10.2.1.01,10.02,7]pentadecan-13-ol by phosphorus oxychloride

  • P. F. Vlad
  • N. D. Ungur
  • A. N. Barba
  • S. T. Malinovskii
  • Yu. A. Simonov
  • T. I. Malinovskii
Article
  • 29 Downloads

Abstract

It has been established that on the dehydration of (1R,2S,7S,10S,12S,13S)-2,6,6,10,12-pentamethyltetracyclo[10.2.1.01,10.02,7]pentadecan-13-ol with phosphorus oxychloride in pyridine a mixture of six substances is formed, from which three previously undescribed hydrocarbons have been isolated and identified: (1R,2S,7S,10S,11R,12S,13S)-2,6,6,10,12-pentamethylpentacyclo[10.2.1.01,10.02,7.-011,13]pentadecane, (1R,2S,7S,10S,12R)-2,6,6,10,13-pentamethyltetracyclo[10.2.1.01,10.02,7]pentadec-13(14)-ene, and (1R,2S,7S,10S,12R)-2,6,6,10-tetramethyltetracyclo[10.2.1.01,10.02,7]pentadec-13(16)-ene, these being based on two new carbon skeletons.

Keywords

Phosphorus Organic Chemistry Hydrocarbon Pyridine Oxychloride 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

  1. 1.
    P. F. Vlad, N. D. Ungur, and M. N. Koltsa, Tetrahedron,39, 3947 (1983).Google Scholar
  2. 2.
    P. F. Vlad, Izv. Akad. Nauk MSSR, Ser. Biol. Khim. Nauk, No. 2, 67 (1977).Google Scholar
  3. 3.
    P. F. Vlad, N. D. Ungur, A. N. Barba, L. E. Tatarova, Yu. V. Gatilov, D. V. Korchagina, I. Yu. Bagryanskaya, V. P. Gatilova, É. N. Shmidt, and V. A. Barkhash, Zh. Org. Khim.,22, 2519 (1986).Google Scholar
  4. 4.
    R. M. Coates and E. E. Bertram, Tetrahedron Lett., No. 49, 5145 (1968).Google Scholar
  5. 5.
    T. Norin and Z. Westfelt, Acta Chem. Scand.,17, 1829 (1963).Google Scholar
  6. 6.
    R. Polyudek-Fabina and T. Beirikh, Organic Analysis [in Russian], Nauka, Leningrad (1981), p. 15.Google Scholar
  7. 7.
    W. Herz and S. V. Govindan, J. Org. Chem.,44, 2999 (1979).Google Scholar

Copyright information

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • P. F. Vlad
  • N. D. Ungur
  • A. N. Barba
  • S. T. Malinovskii
  • Yu. A. Simonov
  • T. I. Malinovskii

There are no affiliations available

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