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

I. Ujváry, A. Kis-Tamás, L. Novák

Research output: Contribution to journalArticle

14 Citations (Scopus)

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 moth Lobesia botrana Schiff.

Original languageEnglish
Pages (from-to)113-124
Number of pages12
JournalJournal of Chemical Ecology
Volume11
Issue number1
DOIs
Publication statusPublished - Jan 1985

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Sex Attractants
Moths
sex pheromone
sex pheromones
moth
moths
acetate
Acetates
acetates
Economics
economics
synthesis
acids
acid
Aldehydes
aldehyde
aldehydes
Acetylation
Nitriles
Lobesia botrana

Keywords

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

ASJC Scopus subject areas

  • Ecology
  • Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

@article{6ef7f0ccf7e044b68d6ebd7ffb8a10a0,
title = "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 moth Lobesia botrana Schiff.",
keywords = "α,β-unsaturated aldehyde, (E,Z)-7,9-dodecadien-1-yl acetate, (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, aleuritic acid, European grapevine moth, Lobesia botrana, Sex pheromone, synthesis, Wittig reaction",
author = "I. Ujv{\'a}ry and A. Kis-Tam{\'a}s and L. Nov{\'a}k",
year = "1985",
month = "1",
doi = "10.1007/BF00987610",
language = "English",
volume = "11",
pages = "113--124",
journal = "Journal of Chemical Ecology",
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TY - JOUR

T1 - 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

AU - Ujváry, I.

AU - Kis-Tamás, A.

AU - Novák, L.

PY - 1985/1

Y1 - 1985/1

N2 - 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 moth Lobesia botrana Schiff.

AB - 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 moth Lobesia botrana Schiff.

KW - α,β-unsaturated aldehyde

KW - (E,Z)-7,9-dodecadien-1-yl acetate

KW - (Z)-7-dodecen-1-yl acetate

KW - (Z)-7-tetradecen-1-yl acetate

KW - (Z)-9-dodecen-1-yl acetate

KW - (Z)-9-tetra-decen-1-yl acetate

KW - aleuritic acid

KW - European grapevine moth

KW - Lobesia botrana

KW - Sex pheromone

KW - synthesis

KW - Wittig reaction

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