Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.tet.2012.03.002
Title: 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
Authors: Shikichi, Y.
Akasaka, K.
Tamogami, S.
Shankar, S.
Yew, J.Y. 
Mori, K.
Keywords: Chemical ecology
Drosophila melanogaster
HPLC separation of E/Z-isomers
HPLC separation of enantiomers
Pheromone
Issue Date: 13-May-2012
Citation: Shikichi, 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
Abstract: All 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.
Source Title: Tetrahedron
URI: http://scholarbank.nus.edu.sg/handle/10635/101374
ISSN: 00404020
DOI: 10.1016/j.tet.2012.03.002
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