A Concise Synthesis of the Natural Mosquito Oviposition Attractant Pheromone from D-Glucose

Abstract

The major component of the oviposition attractant pheromone of the mosquito Culex pipiens fatigans was shown to be (-)-(5R, 6S)-6-acetoxy-5-hexadecanolide (1).1 For the chemical synthesis of this optically active pheromone,2 carbohydrates such as D-mannitol2i and 2-deoxy-D-ribose21 have been utilized as chiral templates. In this laboratory the natural pheromone has been synthesized from (S)- and (R)-O,O-isopropylideneglyceraldehyde independently, using diastereoselective dihydroxylation as the key step.2m We now describe an enantiospecific synthesis of the pheromone from D-glucose.