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Russian Chemical Bulletin

, Volume 47, Issue 8, pp 1595–1597 | Cite as

A versatile approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid

  • G. Yu. Ishmuratov
  • R. Ya. Kharisov
  • M. P. Yakovleva
  • O. V. Botsman
  • R. I. Galeeva
  • N. M. Ishmuratova
  • G. A. Tolstikov
Chemistry of Natural Compounds and Bioorganic Chemistry
  • 42 Downloads

Abstract

A general approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid was developed. The method comprises the conversion of the acid into undec-10-enyl acetate, shortening of its carbon chain to afford dec-9-enyl acetate (via 11-acetoxyundecanoic acid), and a two-step transformation of the latter into the key intermediate, dec-9-yn-1-ol, by sequential bromination—dehydrobromination. The elimination of two HBr molecules from the dibromide is effectively performed using Bu1OK in the presence of dibenzo-18-crown-6 as the catalyst.

Key words

11-acetoxyundecanoic acid dec-9-enyl acetate dec-9-yn-1-ol the Bu1OK-dibenzo-18-crown-6 system pheromones ofLepidoptera 

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Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • G. Yu. Ishmuratov
    • 1
  • R. Ya. Kharisov
    • 1
  • M. P. Yakovleva
    • 1
  • O. V. Botsman
    • 1
  • R. I. Galeeva
    • 1
  • N. M. Ishmuratova
    • 1
  • G. A. Tolstikov
    • 1
  1. 1.Institute of Organic ChemistryUfa Research Center of the Russian Academy of SciencesUfaRussian Federation

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