SYNTHESIS OF THE FOUR POSSIBLE STEREOISOMERS OF N-2′-METHYLBUTYL-2-METHYLBUTYLAMIDE, THE SEX PHEROMONE OF THE LONGHORN BEETLE MIGDOLUS FRYANUS WESTWOOD

Abstract

The four stereoisomers of N-2′-methylbutyl-2-methylbutylamide, the sex pheromone of the longhorn beetle Migdolus fryanus, an economically important pest of sugarcane in South America, were synthesized. The key intermediate 2-methylbutan-1-ol is commercially available only in its (S)-(−)-form. The (R)-(+)-enantiomer was obtained optically pure from methyl (S)-(+)-3-hydroxy-2-methylpropionate in five steps.

ACKNOWLEDGMENTS

The authors are grateful to FAPESP, CNPq (Brazil) and IFS (Sweden) for financial support, and Assoc. Prof. Rikard Unelius for helpful discussions.