Square necked grain pheromone

The male-produced aggregation pheromone of the square-necked grain beetle, Cathartus quadricollis has been identified to be (3R,6 )-3-acetoxy-7-methylnon-6-ene 157 [297]. The compound, termed quadrilure, is attractive to both sexes, however, females are more sensitive at low concentrations. The (S)-enantiomer is biologically inactive. 

Pierce A. M., Pierce H. D., Jr, Johnston B. D., Oehlschlager A. C. and Borden J. H. (1988) Aggregation pheromone of square necked grain beetle, Cathartus quadricollis (GUER). J. Chem. Ecol. 14, 2169-2184. 

In a short formal synthesis of the Californian red scale pheromone 271, Claisen orthoester rearrangement has been employed as a key step [60] (Scheme 6.44). Stereoselective synthesis of the trisubstituted double bond in a component of Caribbean sponge 274 was accomplished with the Claisen-Johnson rearrangement as depicted in Scheme 6.44 [61]. A similar strategy was developed for the stereoselective synthesis of the pheromone 277 of square necked grain (Scheme 6.44) [62]. 

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