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J Chem Ecol

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"
Author(s):		Ujvary I; Kis-Tamas A; Novak L;
Address:		"Department of Organic Chemistry, Plant Protection Institute, Hungarian Academy of Sciences, POB 102, H-1525, Budapest, Hungary"
Journal Title:		J Chem Ecol
Year:		1985
Volume:		11
Issue:		1
Page Number:		113 - 124
DOI:		10.1007/BF00987610
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
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 alpha,beta-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"
Keywords:
Notes:		"PubMed-not-MEDLINEUjvary, I Kis-Tamas, A Novak, L eng 1985/01/01 J Chem Ecol. 1985 Jan; 11(1):113-24. doi: 10.1007/BF00987610"