Total Synthesis of (−)‐Arborisidine
Fengyuan Wang, Lei Jiao
Abstract
An asymmetric total synthesis of cage-like indole alkaloid arborisidine is presented. The new synthetic strategy features a catalytic parallel kinetic resolution based on ambident nucleophilicity (C3/N) of indole to set the absolute configurations of the two quaternary chiral centers, and a 5-exo-trig radical cyclization to form the bridged nitrogen-containing five-membered ring.
Topics & Concepts
Indole testKinetic resolutionChemistryTotal synthesisNucleophileRing (chemistry)StereochemistryIndole alkaloidEnantioselective synthesisCatalysisCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisAlkaloids: synthesis and pharmacology