Pheromone synthesis via organoboranes: A stereoselective synthesis of (E)-1,3-alkenynes via thexylchloroborane-dimethyl sulfide

Abstract

Treatment of thexylalkenylalkynylhoranes with iodine in the presence of potassium methoxide produces (E)-l,3-enynes in good yield (58-82%) and excellent stereochemical purities (≥95 %). The methodology was successfully applied to the synthesis of (5Z,7E)-5,7-dodeeadien-l-ol, the sex pheromone of the forest tent caterpillar (Malacosoma disstria).