Osaka beetle

Japonilure R), the sex pheromone of the female Japanese beetle. Papilla japonica and its enantiomer, (5)-(+)-(5Z )-tetradecen-4-olide, which is the pheromone of the Osaka beetle, Anomala osakana have been synthesized using a highly convergent procedure and in satisfactory overall yields. 

In particular, the importance of chirality in diverse pheromone systems has been reviewed recently (Mori, 1998). For example, olive fruit flies (Bactrocera oleae) emit racemic 2 the males detect the R enantiomer, while females detect the S (Haniotakis et al., 1986). The sex pheromone of the Osaka beetle (Anomala osakana) is 4a, while the closely related Japanese beetle (Popilia japonica) uses 4b (Table 16.1). Interestingly, 4a is a powerful behavioral antagonist in P. japonica (Tumlinson et al., 1977). The hemlock looper, Lambdina fiscellaria, responds only to (5R, 1 S)-5,I I -dimethylheptadecane. The enantiomer or the R/R or S/S diastereomers do not elicit electrophysiological or behavioral responses (Li et al., 1993). Table 16.1 gives an overview of those species where proteins from the pheromone olfactory system have been identified. 

Protein extracts from antennae and legs of the Japanese beetle, the Osaka beetle, Anomala osakana, and the other scarab beetle species (Phyllopertha diversa, Holotrichia parallela, and Exomala orientalis) were incubated either... 

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