A Simple Synthesis of (R)(S)(E)-3,7-Dimethyl-2-octene-1,8-dioc Acid, a Copulation Release Pheromone Component of the Azuki Bean Weevil

Abstract

(R)(S)(E)-3,7-dimethyl-2-octene-1,8-dioic acid, (R)(S)(E)-1, also named callosobruchusic acid, has been synthetized in five steps using a simple reaction sequence based on the zirconium-catalyzed methylalumination of commercially available 4-pentyn-1-ol, 2a, or its O-tert-butyldimethylsilyl ether, 2b.