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. 1984 Jul;10(7):1057-64.
doi: 10.1007/BF00987512.

Pheromone biosynthetic pathways: Conversion of ipsdienone to (-)-ipsdienol, a mechanism for enantioselective reduction in the male bark beetle,Ips paraconfusus

R H Fish  1 , L E Browne, B J Bergot
Affiliations

Pheromone biosynthetic pathways: Conversion of ipsdienone to (-)-ipsdienol, a mechanism for enantioselective reduction in the male bark beetle,Ips paraconfusus

R H Fish et al. J Chem Ecol. 1984 Jul.

Abstract

The enantiomeric composition of the pheromone components (+)-ipsdienoI, e.e. 87.6%, and (-)-ipsenol, e.e. 93.8%, produced by the male bark beetleIps paraconfusus (Scolytidae) under natural conditions was determined by HPLC separation of their diastereomeric ester derivatives. Males confined in an atmosphere of ipsdienone produced (-)-ipsdienol, e.e. 28%, and (-)-ipsenol, e.e. 86%, indicating an enantiomeric selectivity in the conversion of the ketone to the alcohols. These findings demonstrate an enantioselective conversion mechanism in the biosynthetic pathway to the pheromones from myrcene, a host-plant terpene.

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References

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