Stereoselective Tandem Synthesis of Pyrrolidine Derivatives under Gold Catalysis: An Asymmetric Synthesis of (−)-Lepadiformine A
Atsushi Yoshimura, Ryohei Hanzawa, Haruhiko Fuwa
Abstract
A Au-catalyzed tandem alkyne hydroamination/iminium ion formation/allylation reaction was developed for expedient access to pyrrolidine derivatives bearing a tetrasubstituted carbon stereocenter. The tandem reaction was successfully applied to a 12-step asymmetric synthesis of (-)-lepadiformine A, a marine cytotoxic tricyclic alkaloid.
Topics & Concepts
ChemistryPyrrolidineHydroaminationIminiumStereocenterTandemStereoselectivityAlkyneCascade reactionCombinatorial chemistryCatalysisEnantioselective synthesisStereochemistryOrganic chemistryMaterials scienceComposite materialCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods