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|Title:||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|
|Keywords:||(11Z,19Z)-3-Acetoxy-11,19-octacosadien-1-ol, (R)-, (S)-, and (±)-|
3,4-Epoxy-1-butanol PMB ether, (R)-, and (S)-
Jacobsen's hydrolytic kinetic resolution (HKR) of epoxide
|Source:||Mori, K., Shikichi, Y., Shankar, S., Yew, J.Y. (2010-08-28). 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. Tetrahedron 66 (35) : 7161-7168. ScholarBank@NUS Repository. https://doi.org/10.1016/j.tet.2010.06.080|
|Abstract:||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. © 2010 Elsevier Ltd.|
|Appears in Collections:||Staff Publications|
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