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Simple and economic syntheses of some (Z)-7- and (Z)-9-alkenyl acetates, and of (E,Z)-7,9-dodecadien-1-yl acetate, the sex pheromone of the European grapevine moth, using aleuritic acid as a common starting material

Abstract

Short syntheses of (Z)-7-dodecen-1-yl acetate, (Z)-7-tetradecen-1-yl acetate, (Z)-9-dodecen-1-yl acetate, and (Z)-9-tetradecen-1-yl acetate from 7-hydroxyheptanal and 9-oxononanoic acid precursors obtained by oxidative cleavage of easily available aleuritic acid are reported. The key step in these syntheses is a stereoselective Wittig reaction between aldehyde and alkyl-phosphonium salt. Wittig-Horner type reaction of 7-hydroxyheptanal and diethyl cyanomethylphosphonate gave the α,β-unsaturated nitrile derivative which after protection of the hydroxyl group was reduced to the corresponding aldehyde. Wittig reaction of the latter, followed by acetylation, completed the synthesis of (E,Z)-7,9-dodecadien-1-yl acetate, the sex pheromone of the European grapevine mothLobesia botrana Schiff.

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Ujváry, I., Kis-Tamás, A. & Novák, L. Simple and economic syntheses of some (Z)-7- and (Z)-9-alkenyl acetates, and of (E,Z)-7,9-dodecadien-1-yl acetate, the sex pheromone of the European grapevine moth, using aleuritic acid as a common starting material. J Chem Ecol 11, 113–124 (1985). https://doi.org/10.1007/BF00987610

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  • DOI: https://doi.org/10.1007/BF00987610

Key words

  • Sex pheromone
  • synthesis
  • aleuritic acid
  • (Z)-7-dodecen-1-yl acetate
  • (Z)-7-tetradecen-1-yl acetate
  • (Z)-9-dodecen-1-yl acetate
  • (Z)-9-tetra-decen-1-yl acetate
  • (E,Z)-7,9-dodecadien-1-yl acetate
  • European grapevine moth
  • Lobesia botrana
  • Wittig reaction
  • α,β-unsaturated aldehyde