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Scientific article
English

Synthesis of (Z,Z)-3,13-octadecadien-1-yl acetate. Component of the sex pheromone of Synanthedon tenuis

Published inJournal of chemical ecology, vol. 9, no. 2, p. 225-233
Publication date1983
Abstract

The main component of the sex pheromone of the smaller clear wing moth,Synanthedon tenuis, was synthesized. This iterative synthesis uses the carbocupration of acetylene, followed by the alkylation of the (Z)-alkenyl cuprate or by its reaction with ethylene oxide. (Z,Z)-3,13-octadecadien-1-yl acetate, thus obtained, is of 99.8% stereoisomeric purity. An intermediate of the synthesis was (Z)-9-tetradecene-1-yl acetate which is obtained in high yield and 99.9%Z purity.

Keywords
  • Synthesis
  • sex pheromone
  • smaller clear wing moth
  • Synanthedon tenuis Lepidoptera
  • Sessiidae (Z,Z)-3,13-octadecadien-1-yl acetate
  • (Z)-9-tetradecen-1-yl acetate
  • carbocupration
  • alkylation
  • epoxide opening
Affiliation Not a UNIGE publication
Citation (ISO format)
GARDETTE, M., ALEXAKIS, Alexandre, NORMANT, Jean F. Synthesis of (Z,Z)-3,13-octadecadien-1-yl acetate. Component of the sex pheromone of Synanthedon tenuis. In: Journal of chemical ecology, 1983, vol. 9, n° 2, p. 225–233. doi: 10.1007/BF00988040
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ISSN of the journal0098-0331
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