Syntheses of Mersicarpine, a Monoterpenoid Indole Alkaloid with an Atypical Tetracyclic Structure

摘要

The focus review discusses the synthesis of an important member of the monoterpene indole alkaloid family, mersicarpine. Biosynthetically, mersicarpine, isolated from the Kopsia fruticosa and Kopsia arborea, is proposed to share the same biogenetic pathway as melodinine E and leuconolam, and has a fused tetracyclic [6.5.6.7] ring system characterized by an unusual tetrahydro-2H-azepine ring and a hemiaminal motif. As a consequence, this intriguing structural feature has attracted considerable attention from synthetic chemists. The review focuses on the synthesis of mersicarpine from its first synthesis to the most recent one, ranging from 2008-2022.