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Chemistry of Natural Compounds

, Volume 20, Issue 4, pp 486–489 | Cite as

Insect pheromones and their analogues. X. The stereodirected synthesis of (E,E)-dodeca-8,10-dienol

  • V. N. Odinokov
  • G. G. Balezina
  • G. Yu. Ishmuratov
  • I. M. Salimgareeva
  • N. G. Bogatova
  • L. M. Zelenova
  • R. R. Muslukhov
  • G. A. Tolstikov
Article
  • 49 Downloads

Abstract

A passage from deca-1,4,9-triene (I) to (E,E)-dodeca-8,10-dienol (II) in five stages with an overall yield of 23% has been found by the selective transformations of deca-1,4,9-trien-1-yltrimethylsilane. Thus, under mild conditions, by the hydrogenation of (I) with the aid of 9-borabicyclo[3.3.1]nonane (9-BBN) followed by oxidation with H2O2 (E,E)-deca-6,8-dienol was obtained with a yield of 60%, and this was converted quantitatively into the corresponding tosylate. The ethynylation of the latter with lithium acetylide gave (E,E)-dodecadien-1-yne (III) on a Lindlar catalyst followed by the reaction of the resulting triene with 9-BBN, as described above for (I) led to the desired codlemone (II). The IR, PMR,13C NMR, UV, and mass spectra of the compound obtained are discussed.

Keywords

Tosylate Sorbic Acid Sulfonyl Chloride Dienol Piperylene 

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Copyright information

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • V. N. Odinokov
  • G. G. Balezina
  • G. Yu. Ishmuratov
  • I. M. Salimgareeva
  • N. G. Bogatova
  • L. M. Zelenova
  • R. R. Muslukhov
  • G. A. Tolstikov

There are no affiliations available

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