Aggregation pheromone of Gnathotrichus

In 1974, Silverstein and coworkers isolated and identified sulcatol (103, Figure 4.51) as the male-produced aggregation pheromone of Gnathotrichus sulcatus, an economically important ambrosia beetle in the Pacific coast of North America. They showed the natural pheromone to be a 35 65 mixture of (R)-103 and (5)-103 by -NMR analysis of its Mosher ester (a-methoxy-a-trifhioromethylphenylacetate). The reason why the beetle produces a mixture of enantiomers was unclear at the time of its discovery. 

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