Gnathotrichus retusus

Borden J. H. and McLean J. A. (1979) Secondary attraction in Gnathotrichus retusus and cross-attraction of G. sulcatus (Coleoptera Scolytidae)../. Chem. Ecol. 5, 79-88. 

Gnathotrichus retusus. This was synthesized in 73% overall yield from (S)-15 as shown in Figure 5 (13,18). Sulcatol (16) was... 

Gnathotrichus sulcatus produces 6-methyl-5-hepten-2-ol (sulcatol) (229) as its aggregating pheromone, as a 65 35 mixture of 5-(+) and R- —) enantiomers (31S). Borden et al. (316) found that this ambrosia beetle responded maximally to a racemic mixture (50 50) of the two enantiomers. In fact, the response to the racemic mixture was significantly greater than it was to a 65 35 ratio. More recent work, however, suggests that G. sulcatus responds to some extent to 5-(+)-sulcatol alone, that it does not respond to the 5 -(—)-isomer, and that the range of active ratios is much wider than previously indicated (317). In addition, Borden and coworkers (317) have found that G. retusus responds to (5)-(+)-sulcatol in an upwind laboratory bioassay and that the response appears to be inhibited to some extent by the S-(—)-enantiomer. They speculate that speciation may depend in part on the enantiomeric compositions of the pheromone. 

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