EXO- AND ENDOHORMONES XXI: STEREOSELECTIVE SYNTHESIS OF THE FOUR ISOMERS OF THE 4,7-TRIDECADIEN-1-YL ACETATE. (4E,7Z)-4,7-TRIDECADIEN-1-YL ACETATE, THE SEX PHEROMONE OF THE LEAFMINER MOTH PHYLONORYCTER CORYLIFOLIELLA

摘要

The synthesis of the four isomers of 4,7-tridecadien-1-yl acetate, based on a C_5+C_8 scheme is described. The coupling reaction took place between the Grignard reagent of pent-4-yn-1-oic acid and l-bromo-2(Z/E)-octene. The four isomers were separated on SiO_2-AgNO_3 TLC plate and GS-MS. (4E,7Z)-4,7-Tridecadien-1-yl acetate is the sex pheromone of the spottet tentiform leaf miner moth Phylonorycter corylifoliella.