Total synthesis of the monoterpenoid indole alkaloid (±)-aspidophylline A

Abstract

Aspidophylline A belongs to the akuammiline alkaloid family, the members of which possess intriguing cagelike structures and diverse biological activities. Herein we report a 15-step synthesis of this alkaloid from conveniently available starting materials. The key elements of the synthesis include an intramolecular oxidative coupling to create the tetracyclic furoindoline motif of the natural product and a [Ni(cod)2 ]-mediated cyclization to install its piperidine ring.

Keywords: monoterpene indole alkaloids; natural products; nickel; oxidative coupling; total synthesis.