A New Route for the Synthesis of Grapholitha Molesta Sex Pheromone

Chem. J. Chinese Universities ›› 2003, Vol. 24 ›› Issue (6): 1040.

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A New Route for the Synthesis of Grapholitha Molesta Sex Pheromone

LIU Fu-Chu, LI Yan-Wu, LIN Jun, ZHU Hong-You, LI Quan, ZONG Qian-Shou

Department of Applied Chemistry, Yunnan University, Kunming 650091, China

Received:2002-05-21 Online:2003-06-24 Published:2003-06-24
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Abstract

Abstract: The sex pheromone of grapholitha molesta 8(Z/E)-dodecen-1-ol acetate (6) was synthesized bYUsing oleic acids as the raw material. 1,8(Z)-Heptadecadiene (2) was obtained from the decarbonylation reaction of oleic acid (1) in the presence of palladium complexes catalyst. Selective hydroboration and oxidation of 2 by Ca(BH₄₂2O₂ system gave 8(Z)-heptadecen-1-ol (3), which then was acetylized by treatment with Ac 2O/pyridine to afford 8(Z)-heptadecen-ol acetate(4). The compound 4 was ozonized to form the keYINtermediate 8-acetoxyoctanal (5), then compound 5 was coupled with the Wittig regents to obtain the title compound 8(Z/E)dodecen-1-ol acetate (6), Z/E molar ratio is 25;75. The overall yield was 45%. The structures of all the compounds were confirmed by IR, MS and NMR spectra.

Key words: Sex pheromone, Oleic acid, Hydroboration, Ozonization, Wittig reaction

CLC Number:

O623.623

TrendMD:

LIU Fu-Chu, LI Yan-Wu, LIN Jun, ZHU Hong-You, LI Quan, ZONG Qian-Shou . A New Route for the Synthesis of Grapholitha Molesta Sex Pheromone[J]. Chem. J. Chinese Universities, 2003, 24(6): 1040.

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A New Route for the Synthesis of Grapholitha Molesta Sex Pheromone

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