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Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.tet.2012.03.002
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dc.titlePheromone synthesis. Part 250: Determination of the stereostructure of CH503, a sex pheromone of male Drosophila melanogaster, as (3R,11Z,19Z)-3- acetoxy-11,19-octacosadien-1-ol by synthesis and chromatographic analysis of its eight isomers
dc.contributor.authorShikichi, Y.
dc.contributor.authorAkasaka, K.
dc.contributor.authorTamogami, S.
dc.contributor.authorShankar, S.
dc.contributor.authorYew, J.Y.
dc.contributor.authorMori, K.
dc.date.accessioned2014-10-27T08:36:31Z
dc.date.available2014-10-27T08:36:31Z
dc.date.issued2012-05-13
dc.identifier.citationShikichi, Y., Akasaka, K., Tamogami, S., Shankar, S., Yew, J.Y., Mori, K. (2012-05-13). Pheromone synthesis. Part 250: Determination of the stereostructure of CH503, a sex pheromone of male Drosophila melanogaster, as (3R,11Z,19Z)-3- acetoxy-11,19-octacosadien-1-ol by synthesis and chromatographic analysis of its eight isomers. Tetrahedron 68 (19) : 3750-3760. ScholarBank@NUS Repository. https://doi.org/10.1016/j.tet.2012.03.002
dc.identifier.issn00404020
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/101374
dc.description.abstractAll the eight stereoisomers of 3-acetoxy-11,19-octacosadien-1-ol (1), the male sex pheromone (CH503) of Drosophila melanogaster, were synthesized from two acetylenic starting materials and the enantiomers of 3,4-epoxy-1-butanol PMB ether. Complete separation of the eight isomers of 1 by reversed phase HPLC at -20 °C was achieved after their esterification with (1R,2R)-2-(2,3- anthracenedicarboximido)cyclohexanecarboxylic acid (27), and the natural CH503 was found to be (3R,11Z,19Z)-1. © 2012 Elsevier Ltd. All rights reserved.
dc.description.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1016/j.tet.2012.03.002
dc.sourceScopus
dc.subjectChemical ecology
dc.subjectDrosophila melanogaster
dc.subjectHPLC separation of E/Z-isomers
dc.subjectHPLC separation of enantiomers
dc.subjectPheromone
dc.typeArticle
dc.contributor.departmentBIOLOGICAL SCIENCES
dc.description.doi10.1016/j.tet.2012.03.002
dc.description.sourcetitleTetrahedron
dc.description.volume68
dc.description.issue19
dc.description.page3750-3760
dc.description.codenTETRA
dc.identifier.isiut000303303400010
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