SYNTHESIS OF THE ENANTIOMERS OF CIS-2-METHYL-5-HEXANOLIDE, THE MAJOR COMPONENT OF THE SEX PHEROMONE OF THE CARPENTER BEE

Article abstract of DOI:10.1016/S0040-4020(01)96497-X

(2R,5S)-2-Methyl-5-hexanolide and its antipode were synthesized in highly optically pure state (<*>98-99percent e.e.) starting from ethyl (S)-lactate and the enantiomers of methyl β-hydroxyisobutyrate.The specific rotations of our samples were <α>_D +/- 91.0 -93.5 deg (CHCl3), while the reported values of the samples prepared by resolution or asymmetric synthesis were +/- 64.5-65.6 deg.