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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

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

J Chem Ecol. 1985 Jan;11(1):113-24.

PMID: 24311103

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP533879	Aleuritic acid		533-87-9	Price

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