Propylure synthesis

The isolation of the pheromone obtained from the female of the pink bollworm, Pectinophora gossypiella, and the determination of the structure and synthesis of the compound are also associated with the names of Jacobson and co-workers (Jones era/., 1966). The synthetic ( )-10-propyl-5-tridecadienyl acetate (propylure,... 

Modification of the propylure (4) molecule resulted in the synthesis of a mixture of geometrical isomers of 5,9-tridecadienyl acetate (20). This product has an attractant effect on several agricultural insect pests (Warthon and Jacobson, 1967). 

Among many other syntheses involving extensive use of ylides are those of lycoxanthin, /8,y- and y,y-carotene, 10,ll 10, ir-bisdehydrorhodo-xanthin, ethyl ( —)-abscisate, propylure, and of juvenile hormone. In the course of the last mentioned, the phosphonium salts (107 X = H or SiMea) were used successfully in olefin synthesis, but reactions involving the salt (107 X = CHgOH) were not successful. 

The reaction has been applied to a synthesis of propylure, the sex attractant of the pink bollworm moth. ... 

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