| Title: | "Synthesis of the four stereoisomers of 7-acetoxy-15-methylnonacosane, a component of the female sex pheromone of the screwworm fly, Cochliomyia hominivorax" |
| Author(s): | Mori K; Ohtaki T; Ohrui H; Berkebile DR; Carlson DA; |
| Address: | "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" |
| Journal Title: | Biosci Biotechnol Biochem |
| ISSN/ISBN: | 0916-8451 (Print) 0916-8451 (Linking) |
| 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" |
| Keywords: | Alkanes/*chemical synthesis/chemistry Animals Diptera/*chemistry Female Pheromones/*chemical synthesis/chemistry Stereoisomerism; |
| Notes: | "MedlineMori, Kenji Ohtaki, Takashi Ohrui, Hiroshi Berkebile, Dennis R Carlson, David A eng England 2004/08/24 Biosci Biotechnol Biochem. 2004 Aug; 68(8):1768-78. doi: 10.1271/bbb.68.1768" |
