Entomology, Department of
Synthesis of the Four Stereoisomers of 7-Acetoxy-15-methylnonacosane, a Component of the Female Sex Phermone of the Screwworm Fly, Cocliomyia hominivorax)
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The four stereoisomers of 7-acetoxy-15-methylnonacosane (1), a component of the female sex pheromone of the New World screwworm fly (Cocliomyia 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 (13). Three of the stereoisomers of 1 showed equivalent good pheromone activity, while the activity of (7R,15R)-1 was weak.
Published in Biosci. Biotechnol. Biochem., 68 (8), 1768-1778, 2004.