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J Chem Ecol

Title:		"Synthesis of the stereoisomers of the female sex pheromone of the Hessian fly,Mayetiola destructor"
Author(s):		Millar JG; Foster SP; Harris MO;
Address:		"Department of Entomology, University of California, 92521, Riverside, California"
Journal Title:		J Chem Ecol
Year:		1991
Volume:		17
Issue:		12
Page Number:		2437 - 2447
DOI:		10.1007/BF00994592
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"The female-produced sex pheromone of the Hessian fly,Mayetiola destructor (Say) (Diptera: Cecidomyiidae), has been identified as (10E)-tridecen-2-yl acetate. A flexible synthetic route was developed which allowed access to the chiral and racemic forms of the pheromone, and to the 10Z stereoisomer of the pheromone. The natural compound was determined to have the 2S configuration by hydrolysis of the acetate function, derivatization of the resulting alcohol with (2S)-2-acetoxypropionyl chloride, and capillary gas Chromatographic comparison of the derivative with the corresponding derivatives prepared from the synthetic enantiomers. Trace amounts of the 10Z isomer of the pheromone have also been detected in extracts of female Hessian fly ovipositors, along with (10E)-tridecen-2-ol and 2-tridecanyl acetate. Due to the small quantities of these compounds available from ovipositor extracts, the chirality of the trace components has not yet been determined"
Keywords:
Notes:		"PubMed-not-MEDLINEMillar, J G Foster, S P Harris, M O eng 1991/12/01 J Chem Ecol. 1991 Dec; 17(12):2437-47. doi: 10.1007/BF00994592"