A versatile cascade of intramolecular Vilsmeier-Haack and azomethine ylide 1,3-dipolar cycloaddition toward tricyclic cores of alkaloids.
In the pursuit of synthetic efficiency, we developed an innovative one-pot transformation of linear substrates into bi- and tricyclic adducts using a cascade of amide activation, nucleophilic cyclization, azomethine ylide generation, and subsequent inter- or intramolecular 1,3-dipolar cycloaddition. Despite the high density and variety of functional groups on the substrates, the sequence occurred with perfect chemoselectivity with good to excellent yields.
Département de Chimie, Université de Sherbrooke, 2500 boulevard Université, Sherbrooke, Québec J1K 2R1, Canada.
François
F
Lévesque
Guillaume
G
Bélanger