Enantiomeric synthesis of dominicalure, aggregation pheromone of lesser grain borer,Rhyzopertha dominica (F.).

(S)-(+)-1-Methylbutyl (E)-2-methyl-2-pentenoate,1, and (S)-(+)-1-methylbutyl (E)-2,4-dimethyl-2-pentenoate2, the aggregation pheromone for lesser grain borerRhyzopertha dominica (F). were synthesized from crotylaldehyde in an overall yield of 30%. The chiral intermediate6 was prepared in 90% enantiomer excess, employing the Sharpless asymmetric epoxidation.