Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.tet.2010.06.080
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
Authors: Mori, K.
Shikichi, Y.
Shankar, S.
Yew, J.Y. 
Keywords: (11Z,19Z)-3-Acetoxy-11,19-octacosadien-1-ol, (R)-, (S)-, and (±)-
3,4-Epoxy-1-butanol PMB ether, (R)-, and (S)-
Drosophila melanogaster
Jacobsen's hydrolytic kinetic resolution (HKR) of epoxide
Pheromone
Issue Date: 28-Aug-2010
Citation: 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.
Source Title: Tetrahedron
URI: http://scholarbank.nus.edu.sg/handle/10635/101373
ISSN: 00404020
DOI: 10.1016/j.tet.2010.06.080
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