Synthesis of the four stereoisomers of 7-acetoxy-15-methylnonacosane, a component of the female sex pheromone of the screwworm fly, Cochliomyia hominivorax.
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.
Mori
Kenji
K
Insect Pheromone and Traps Division, Fuji Flavor Co., Ltd., Midorigaoka 3-5-8, Hamura-shi, Tokyo 205-8503, Japan. kjk-mori@arion.ocn.ne.jp
Ohtaki
Takashi
T
Ohrui
Hiroshi
H
Berkebile
Dennis R
DR
Carlson
David A
DA
D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D004175:Diptera / Q000737:chemistry*; D005260:Female; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C497665:7-acetoxy-15-methylnonacosane; D000473:Alkanes; D010675:Pheromones