1374014-95-5Relevant articles and documents
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
Shikichi, Yasumasa,Akasaka, Kazuaki,Tamogami, Shigeyuki,Shankar, Shruti,Yew, Joanne Y.,Mori, Kenji
, p. 3750 - 3760 (2012/06/30)
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.