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J Agric Food Chem

Title:		"Improved synthesis of (3E,7Z)-3,7-tetradecadienyl acetate, the major sex pheromone constituent of the potato pest Symmetrischema tangolias (Gyen)"
Author(s):		Ragoussis V; Perdikaris S; Karamolegkos A; Magkiosi K;
Address:		"Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis Zographou, 157 71 Athens, Greece. ragousi@chem.uoa.gr"
Journal Title:		J Agric Food Chem
Year:		2008
Volume:		56
Issue:		24
Page Number:		11929 - 11932
DOI:		10.1021/jf802473m
ISSN/ISBN:		1520-5118 (Electronic) 0021-8561 (Linking)
Abstract:		"An efficient six-step synthesis of (3E,7Z)-3,7-tetradecadienyl acetate, the major component of the sex pheromone of the potato pest Symmetrischema tangolias (Gyen), is described, starting from the commercially available dihydropyran. The stereoselective formation of the 7Z double bond is accomplished by a Wittig reaction, while the 3E double bond is formed by a modified Knoevenagel condensation. The overall yield of the synthesis is 28%, giving the final product in high stereochemical purity (95%). The simplicity and the low cost of the herein reported synthesis suggest the potential practical use of the above pheromone in integrated management programs, for this serious insect pest"
Keywords:		Animals Moths/*chemistry/metabolism Plant Diseases/*parasitology Sex Attractants/*chemical synthesis/chemistry Solanum tuberosum/*parasitology;
Notes:		"MedlineRagoussis, Valentine Perdikaris, Stamatis Karamolegkos, Antonis Magkiosi, Konstantina eng 2008/12/05 J Agric Food Chem. 2008 Dec 24; 56(24):11929-32. doi: 10.1021/jf802473m"