Synthesis of the Four Stereoisomers of 7-Acetoxy-15-methylnonacosane, a Component of the Female Sex Phermone of the Screwworm Fly, Cocliomyia hominivorax)

Authors

• Kenji Mori, Insect Pheromone and Traps Division, Fuji Flavor Co., Ltd., Midorigaoka 3-5-8, Hamura-shi, Tokya 205-8503, Japan
• Takashi Ohtaki, Tohoku University, Tsutsumidori-Amamiya 1-1, Aoba-ku, Sendai 981-8555, Japan
• Hiroshi Ohrui, Tohoku University, Tsutsumidori-Amamiya 1-1, Aoba-ku, Sendai 981-8555, Japan
• Dennis Berkebile, USDA-ARSFollow
• David A. Carlson, USDA-ARS

Document Type

Article

Date of this Version

May 2004

Comments

Published in Biosci. Biotechnol. Biochem., 68 (8), 1768-1778, 2004.

Abstract

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.