- Synthesis of (4R,9Z)-9-octadecen-4-olide, the female sex pheromone of Janus integer, and its enantiomer
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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.
- Shibata, Chie,Mori, Kenji
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p. 1083 - 1088
(2007/10/03)
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- A convenient chiral synthesis of 4-alkyl-γ-butanolides
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A simple three step synthesis of 4-alkyl-γ-butanolides as flavoring compounds from chiral propargyl alcohols is described.
- Yadav,Maniyan
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p. 2731 - 2741
(2007/10/02)
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