Synthesis of (4R,9Z)‐9‐Octadecen‐4‐olide, the Female Sex Pheromone of Janus integer, and Its Enantiomer
@article{Shibata2004SynthesisO,
title={Synthesis of (4R,9Z)‐9‐Octadecen‐4‐olide, the Female Sex Pheromone of Janus integer, and Its Enantiomer},
author={Chi{\'e} Shibata and K. Mori},
journal={European Journal of Organic Chemistry},
year={2004},
volume={2004},
pages={1083-1088}
}Enantiomer separation of (±)-8-tert-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… CONTINUE READING
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