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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. KGaA, 69451 Weinheim, Germany, 2004)
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Shibata et al. (2004) studied this question.
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