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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 |
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| Authors: | Kenji Mori Yasumasa Shikichi Joanne Y. Yew |
| Affiliation: | a Photosensitive Materials Research Center, Toyo Gosei Co., Ltd, Wakahagi 4-2-1, Inzai-shi, Chiba 270-1609, Japan b Temasek Life Sciences Laboratory, 1 Research Link, National University of Singapore, Singapore 117604 c Department of Biological Sciences, 14 Science Drive 4, National University of Singapore, Singapore 117546 |
| 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. |
| Keywords: | (11Z,19Z)-3-Acetoxy-11,19-octacosadien-1-ol, (R)-, (S)-, and (± )- Drosophila melanogaster 3,4-Epoxy-1-butanol PMB ether, (R)-, and (S)- Jacobsen&rsquo s hydrolytic kinetic resolution (HKR) of epoxide Pheromone |
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