The copulation release pheromone of the azuki bean weevil, Callosobyuchus chinensis L., erectin, was identified by us1) as the mixture of Callosobruchusic acid and several hydrocarbons: 3-methylpentacosane, 11-methylheptacosane, 3-methylheptacosane, 11-methylnonacosane, 13-methylnonacosane, 11, 15-dimethylnonacosane, 13-methylhentriacontane, 9, 13-dimethylhentriacontane and 11, 15-dimethyltritriacontane. The synthesis of the hydrocarbon components will be reported elsewhere, because they are the common components of oviposition marking pheromone of the azuki bean weevil. This paper, therefore, reports the synthesis of Callosobruchusic acid and its biological activity as a part of its structural assignment as (E)-3,7-dimethyl-2octenedioic acid (I). Glc conditions for separation and characterization were: 2 m x 3 mm glass column; Uniport KA (80-100 mesh) as support; 15% DEGS as stationary phase; 70 ml/ min of nitrogen; column temperature, 220C, on Shimadzu GC 6A. Rt is given in min. The synthetic scheme is outlined in Fig. 1. Geranyl acetate (II) was converted via III to a crude mixture containing 46% of IV (Rt, 2.1) and 36% of V (Rt, 3.7) according to Meinwald et al. 2) The mixture was oxidized in acetone with Jones reagent to give an oily product containing 79% of VI as determined by glc of the methyl ester (VIa). A portion was purified by column chromatography.
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