Stereoselective synthesis of the major component of a mosquito oviposition attractant pheromone from a β-lithiopropionate equivalent

Abstract

β-Lithiated β-ethylthioacrylate 5 A is a versatile β-lithiopropionate equivalent. Reaction with enantiomerically pure epoxide (-)- 4 and subsequent Raney nickel treatment gives the natural oviposition attractant pheromone of the mosquito Culex pipiens fatigans (-)- 1 . From epoxide (+)- 4 the enantiomer (+)- 1 is synthesized.