A novel synthesis of (−)-callicarpenal.

Abstract Callicarpenal, isolated from the leaves of American beautyberry ( Callicarpa americana ) and Japanese beautyberry ( Callicarpa japonica ), exhibits significant mosquito bite-deterring activity and repellent activity against ticks and fire ants. The mosquito bite-deterring activity level of callicarpenal was reported to be similar to that of N , N -diethyl- m -toluamide. The novel synthesis of (−)-callicarpenal reported herein was accomplished by starting from (+)-pulegone. In our original approach, a novel Prins-type cyclization based on Meyer–Schuster rearrangement was featured as a key step. Graphical abstract Image 1 Highlights • A novel synthesis of (−)-callicarpenal was achieved. • Callicarpenal is a tetranorditerpene aldehyde with a potent mosquito repellent activity. • Prins-type cyclization based on Meyer-Schuster rearrangement was featured as a key step. [ABSTRACT FROM AUTHOR]