CHIRAL SYNTHESIS OF (2S,3S,7S)-3,7-DIMETHYLPENTADECAN-2-YL ACETATE AND PROPIONATE, POTENTIAL SEX PHEROMONE COMPONENTS OF THE PINE SAW-FLY NEODIPRION SERTIFER (GEOFF.)

Article abstract of DOI:10.1016/S0040-4020(01)97980-3

A synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate (2) and propionate (3) is described. (2S)-2-Methyldecan-1-yl lithium (5) was reacted with (3S,4S)-3,4-dimethyl-γ-butyrolactone (6) to yield the ketoalcohol 19 which upon Huang-Minlon reduction furnished (2S,3S,7S)-3,7-dimethylpentadecan-2-ol (1).Acylations gave the esters 2 and 3.The (2S)-2-methyldecan-1-yl lithium was obtained via asymmetric synthesis.The chiral lactone 6 was obtained from (2S,3S)-trans-2,3-epoxybutane and dimethylmalonate.