Synthesis of the four stereoisomers of 7-acetoxy-15-methylnonacosane, a component of the female sex pheromone of the screwworm fly, Cochliomyia hominivorax.
Authors:
Mori, K. Ohtaki, T. Ohrui, H. Berkebile, D.R. Carlson, D.A. USDA, ARS
Source:
Bioscience, biotechnology, and biochemistry. 2004 Aug., v. 68, no. 8, p. 1768-1778.
NALT Subjects:
Cochliomyia hominivorax females sex pheromones chemical structure stereoisomers synthesis bioactive properties sex attractants
Issue Date:
Aug-2004
Abstract:
The four stereoisomers of 7-acetoxy-15-methylnonacosane (1), 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 (13). Three of the stereoisomers of 1 showed equivalent good pheromone activity, while the activity of (7R,15R)-1 was weak.
