Popillia japonica Japonilure

Enantiomerically pure japonilure [(4JR,5Z)-5-tetradecen-4-olide, 26] is commercially important to attract the Japanese beetle (Popillia japonica), because only pure (4.R,5Z)-26 is bioactive, while ( )-26 is totally inactive. Synthesis of (4 ,5Z)-26 via enzymatic resolution of racemic intermediates was first reported by Sugai [63], and then further studied by Fukusaki [64] to establish the process as summarized in Scheme 39. Lipase PS (Amano) from Pseudomonas sp. and lipase OF (Meito) from Candida cylindracea were shown to be the enzymes of choice. 

Females of several species use (R)-5-[(lZ)-l-octenyl]oxacyclopentan-2-one, buibuilactone 69 [ 140-144]. The first y-lactone identified from a scarab beetle was (R)-5-[(Z)-l-decenyl]oxacyclopentan-2-one, japonilure 70, the female produced sex pheromone of the Japanese beetle Popillia japonica [145]. Both 69 and 70 are components of specific blends of several species [140-143]. The Japanese beetle is extremely sensitive to the non-natural enantiomer of his pheromone as little as 1% of the (S)-enantiomer inhibits the attractiveness of the pheromone [ 145]. With respect to species discrimination, this is particularly... 

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