Concise synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate and (3E,8Z)-tetradeca-3,8-dienyl acetate, both sex pheromone components of the tomato leafminer Tuta absoluta

Abstract

A highly efficient and concise synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate (1) and (3E,8Z)-tetradeca-3,8- dienyl acetate (2), both sex pheromone components of the tomato leafminer Tuta absoluta was achieved. The stereoselective formation of the 8Z-double bond was accomplished by a Wittig reaction and the 3E-double bond was formed by a modified Knoevenagel condensation. Pheromones 1 and 2 were obtained in high stereochemical purity, and starting from commercially available hexane-1,6-diol, both overall yield were 34.7% and 37.6%, respectively.