An improved and convenient new synthesis of the pheromone components of the tomato leafminer Tuta absoluta

Abstract

A C6 + C4 + C4 regiodivergent synthesis of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate (1) and (3E,8Z)-3,8-tetradecadienyl acetate (2), the major and minor sex pheromone components of the tomato leafminer Tuta absoluta, has been developed. The route employs alkylation of THP-protected 4-bromo-1-butanol followed by Wittig reactions, enabling preparation of each pheromone in seven steps (longest linear sequence).