Cathartus quadricollis Quadrilure

The procedure has been used in a variety of syntheses of natural products [143, 144] for example, in the synthesis of dihydroxyserrulatic acid (Scheme 2-50) [145], the aggregation pheromone of Cathartus quadricollis (quadrilure) [146], and aza-C-disaccharides [147]. 

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. 

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