ARS | Publication request: SYNTHESIS OF THE FOUR STEREOISOMERS OF 7-ACETOXY-15-METHYLNONACOSANE, A COMPONENT OF THE FEMALE SEX PHEROMONE OF THE SCREWWORM FLY, COCHLIOMYIA HOMINIVORAX

Submitted to: Bioscience Biotechnology and Biochemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: May 13, 2004
Publication Date: July 1, 2004
Citation: Mori, K., Ohtaki, T., Ohrui, H., Berkebile, D.R., Carlson, D.A. 2004. Synthesis of the four stereoisomers of 7-acetoxy-15-methylnonacosane, a component of the female sex pheromone of the screwworm fly, cochliomyia hominivorax. Bioscience Biotechnology and Biochemistry. v. 68(8). pp 1768-1778.

Interpretive Summary: The New World Screwworm fly remains a destructive pest of cattle and other mammals in several Caribbean nations and in all of South America, despite its eradication by USDA and IAEA sterile male release projects in North and Central America. A study of synthetic sex pheromone candidates was made using bioassays of synthetic chemicals in tests against colonized male New World Screwworm flies. A scientist at the Center for Medical, Agricultural and Veterinary Entomology, Gainesville Florida and another at the Midwest Livestock Insect Research Unit, Lincoln, Nebraska conducted bioassays with these flies. The tests show excellent biological activity including mating attempts, using specially synthesized optically-active isomers of 7-acetoxy-15-methylnonacosane when tested at 1 ug or more against fertile males of one colonized strain. The compounds had been synthesized by Dr. K. Mori, Fuji Flavors Company, Japan for this important international effort. Research efforts continue in the search for attractive chemicals that can be used against these destructive insects using traps.

Technical Abstract: The four stereoisomers of 7-acetoxy-15-methylnonacosane, a component of the female sex pheromone of the New World screwworm fly (Cochliomyia hominivorax) were synthesized. The stereogenic center at C-15 of 1 originated from that of the enantiomers of citronellal, and that at C-7 was generated by lipase-catalyzed asymmetric acetylation of (3RS,11R)- and (3RS,11S)-17- methyl-1-trimethylsilylpentacos-1-yn-3-ol. Three of the stereoisomers of 1 showed equivalent good pheromone activity, while the activity of (7R,15R)-1 was weak.