Total Synthesis of (−)-Strempeliopine

Abstract

A total synthesis of (-)-strempeliopine is disclosed that enlists a powerful SmI₂-mediated and BF₃·OEt₂-initiated dearomative transannular radical cyclization onto an indole by an <i>N</i>-acyl α-aminoalkyl radical that is derived by single electron reduction of an in situ generated iminium ion for formation of a quaternary center and the strategic C19-C2 bond in its core structure.