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

作者：Shikichi Yasumasa; Akasaka Kazuaki; Tamogami Shigeyuki; Shankar Shruti; Yew Joanne Y; Mori Kenji^*

来源：Tetrahedron, 2012, 68(19): 3750-3760.

DOI：10.1016/j.tet.2012.03.002

• Chemical ecology
• Drosophila melanogaster
• HPLC separation of enantiomers
• HPLC separation of E/Z-isomers
• Pheromone

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 degrees 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,11Z19Z)-1.

• 出版日期2012-5-13