685835-08-9Relevant academic research and scientific papers
Synthesis of (4R,9Z)-9-octadecen-4-olide, the female sex pheromone of Janus integer, and its enantiomer
Shibata, Chie,Mori, Kenji
, p. 1083 - 1088 (2004)
Enantiomer separation of (±)-8-fert-butyldiphenylsilyloxy-1-octyn-3- ol was achieved by lipase-mediated asymmetric acetylation. The resolved (R)-alkynol was converted into (4R,9Z)-9-octadecen-4-olide, which was identical with the female sex pheromone of the currant stem girdler (Janus integer). The absolute configuration of the natural pheromone was thus established as R. (4S,9Z)-9-Octadecen-4-olide was also synthesized, and found to be pheromonally inhibitory. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
