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.)

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