Syntheses of Diverse Natural Products via Dual-Mode Lewis Acid Induced Cascade Cyclization Reactions

Abstract

The σ/π-binding properties of a series of Lewis acids was studied using DFT calculations. The results led to the identification of Zn(II)/In(III) as a suitable dual-mode Lewis acid for use in promoting cascade cyclization reactions. Based on this finding, we developed three new types of dual-mode Lewis acid induced cascade cyclization reactions and have demonstrated the utilities of each process in natural product synthesis. 1 Introduction 2 Dual-Mode Lewis Acids 3 Prins/Conia-Ene Cascade Reaction and its Applications 4 Diels–Alder/Carbocyclization Cascade Reaction and Applications 4.1 First Generation Diels–Alder/Carbocyclization Cascade Reaction and its Application 4.2 Second Generation Diels–Alder/Carbocyclization Cascade Reaction and its Applications 5 Michael/Conia-Ene Cascade Reaction and its Applications 6 Conclusion