Simple and economic syntheses of some (Z)-7- and (Z)-9-alkenyl acetates,and of (E,Z)-7,9-dodecadien-1-yl acetate,the sex pheromone of the European grapevine moth,using aleuritic acid as a common starting material |
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Authors: | I Ujváry A Kis-Tamás L Novák |
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Affiliation: | (1) Department of Organic Chemistry, Plant Protection Institute, Hungarian Academy of Sciences, POB 102, H-1525 Budapest, Hungary;(2) EGyT Pharmacochemical Works, POB 100, H-1475 Budapest, Hungary;(3) Institute for Organic Chemistry, Technical University, Gellért tér 4., H-1521 Budapest, Hungary |
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Abstract: | Short syntheses of (Z)-7-dodecen-1-yl acetate, (Z)-7-tetradecen-1-yl acetate, (Z)-9-dodecen-1-yl acetate, and (Z)-9-tetradecen-1-yl acetate from 7-hydroxyheptanal and 9-oxononanoic acid precursors obtained by oxidative cleavage of easily available aleuritic acid are reported. The key step in these syntheses is a stereoselective Wittig reaction between aldehyde and alkyl-phosphonium salt. Wittig-Horner type reaction of 7-hydroxyheptanal and diethyl cyanomethylphosphonate gave the ,-unsaturated nitrile derivative which after protection of the hydroxyl group was reduced to the corresponding aldehyde. Wittig reaction of the latter, followed by acetylation, completed the synthesis of (E,Z)-7,9-dodecadien-1-yl acetate, the sex pheromone of the European grapevine mothLobesia botrana Schiff. |
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Keywords: | Sex pheromone synthesis aleuritic acid (Z)-7-dodecen-1-yl acetate (Z)-7-tetradecen-1-yl acetate (Z)-9-dodecen-1-yl acetate (Z)-9-tetra-decen-1-yl acetate (E Z)-7 9-dodecadien-1-yl acetate European grapevine moth Lobesia botrana Wittig reaction " target="_blank">gif" alt="agr" align="BASELINE" BORDER="0"> -unsaturated aldehyde" target="_blank">gif" alt="beta" align="MIDDLE" BORDER="0">-unsaturated aldehyde |
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