Total Synthesis of (−)-Strempeliopine
Xianhuang Zeng, Dale L. Boger
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 N-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.
Topics & Concepts
ChemistryIminiumTotal synthesisIndole testStereochemistryIonMedicinal chemistryCombinatorial chemistryOrganic chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions