A protecting group-free synthesis of the Colorado potato beetle pheromone

Abstract

A novel synthesis of the aggregation pheromone of the Colorado potato beetle, Leptinotarsa decemlineata, has been developed based on a Sharpless asymmetric epoxidation in combination with a chemoselective alcohol oxidation using catalytic [(neocuproine)PdOAc]2OTf2. Employing this approach, the pheromone was synthesized in 3 steps, 80% yield and 86% ee from geraniol.

Keywords

• aggregation pheromone
• catalysis
• Colorado potato beetle
• Leptinotarsa decemlineata
• oxidation
• natural product