Pheromone Synthesis via Organoboranes: A stereoselective Synthesis of (E)-1,3-Alkenynes via Thexylchloroborane-Dimethyl Sulfide

Article abstract of DOI:10.1055/s-1986-31746

Treatment of thexylalkenylalkynylboranes with iodine in the presence of potassium methoxide produces (E)-1,3-enynes in good yield (58-82percent) and excellent stereochemical purities (>=95percent).The methodology was successfully applied to the synthesis of (5Z,7E)-5,7-dodecadien-1-ol, the sex pheromone of the forest tent caterpillar (Malacosoma disstria).