Pheromone synthesis. Part 244: Synthesis of the racemate and enantiomers of (11Z,19Z)-CH503 (3-acetoxy-11,19-octacosadien-1-ol), a new sex pheromone of male Drosophila melanogaster to show its (S)-isomer and racemate as bioactive

• DOI: 10.1016/j.tet.2010.06.080
• Publication Date: 2010-07-04T08:12:29Z
• Authors: Kenji Mori; Yasumasa Shikichi; Shruti Shankar; Joanne Y. Yew
• Keywords: 0301 basic medicine; 570; 0303 health sciences; Pheromone; and (S)-; 540; 03 medical and health sciences; (R)-; Drosophila melanogaster; and (±)-; Jacobsen's hydrolytic kinetic resolution (HKR) of epoxide; (S)-; (11Z,19Z)-3-Acetoxy-11,19-octacosadien-1-ol; 3,4-Epoxy-1-butanol PMB ether

The enantiomers of (11Z,19Z)-3-acetoxy-11,19-octacosadien-1-ol were synthesized from the enantiomers of 3,4-epoxy-1-butanol PMB ether. Its racemate was also synthesized. Its (S)-isomer and racemate were shown to possess the same pheromone activity as CH503, a long-lived inhibitor of male courtship in Drosophila melanogaster, although the racemate was less active.