Synthesis of the sex pheromone of the peach fruit moth, Carposina sasakii Matsumura

The peach fruit moth (Carposina sasakii Matsumura) is one of China's most serious fruit-boring pests. Sex pheromone-based pest control has the advantages of being highly efficient, environmentally benign and rarely inducing pest resistance. However, the sex pheromone of the peach fruit moth, (Z)-12-decadecadecene-9-one and (Z)-13-decadecene-10-one, is extremely low in the pest. Therefore, it is insufficient for large-scale pest control via artificial extraction. An efficient synthesis of the sex pheromone has been developed via 7 steps including tetrahydro-2H-pyran-2-yl (THP) protection, nucleophilic substitution, Brown P2-Ni reduction, the addition of Grignard reagent and the oxidation with pyridinium dichromate (PDC) from 3-bromopropan-1-ol. Notably, Brown P2-Ni reduction was firstly used to construct a carbon-carbon double bond of the sex pheromone.The total yield was 5%. Our study has the advantages of simple operation and target pheromone with high regional selectivity (Z: E > 99:1), which could be used for the green control of the peach fruit moth.