Practical synthesis of the main sex pheromones of pine sawflies (2S,3S,7S)-3,7-dimethylpentadecan-2-ol esters by utilizing (R)-4-methyl-delta-valerolactone obtained from the industrial waste

The synthesis of the sex pheromones of pine sawflies (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate (2) and its propionate (3) by utilizing the industrial waste, (R)-4-methyl-6-valerolactone in the degradation of steroidal sapogenin was first reported in this paper. (R)-4-Methyl-b.-Valerolactone was transformed into (R)-methyl 5-bromo-4-methylpentanoate (5) which is a stable and easily reserved reagent. 5 then underwent a series of reaction involving coupling, reduction, bromination and addition to epoxide to give target molecules 2 and 3. This research result not only provides a concise synthetic method for (2S,3S,7S)-3,7-dimethylpentadecan-2-yI acetate (2) and propionate (3), but also enrichs the connotation of resource chemistry (the organic synthetic chemistry based on the rational utilization of resource compounds). Keywords