Improved synthesis of (3E,7Z)-3,7-tetradecadienyl acetate, the major sex pheromone constituent of the potato pest Symmetrischema tangolias (Gyen).
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.
Ragoussis
Valentine
V
Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis Zographou, 157 71 Athens, Greece. ragousi@chem.uoa.gr
Perdikaris
Stamatis
S
Karamolegkos
Antonis
A
Magkiosi
Konstantina
K
D000818:Animals; D009036:Moths / Q000737:chemistry* / Q000378:metabolism; D010935:Plant Diseases / Q000469:parasitology*; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry; D011198:Solanum tuberosum / Q000469:parasitology*
C505894:(9Z, 11E)-tetradecadienyl acetate; D012724:Sex Attractants