A Concise Asymmetric Synthesis of (2S, 3S, 7S)-3,7-Dimethylpentadecan-2-yl Acetate and Propionate, the Sex Pheromones of Pine Sawflies

摘要

(2S, 3S, 7S)-3,7-Dimethylpentadecan-2-yl acetate (2) and its propionate analogue (3) are the main sex pheromones of all Neodiprion species and Diprion similes, respectively. Starting from (S)-malic acid and employing a highly chemo, regio-, and stereoselective tandem ester reduction―epoxide formation―reductive epoxide-opening reaction protocol, an efficient total synthesis of (2S,3S,7S)-2 and -3 is reported herein.