Efficient synthesis of beetle aggregation pheromone frontalin and its analogues

(−)-Frontalin is an aggregation pheromone that has found application in selective exterminating of certain harmful insects. This paper discloses an expedite synthesis of (±)-frontalin from a symmetric molecule, 2,6-dimethyl-1,6-heptadiene, in 64% yield. The one-flask operation consists of double dihydroxylation, mono-cleavage, and acid-catalyzed intramolecular acetalation. Our unique strategy was also successfully applied to additional diene substrates such as and .