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

Key words

dual-mode - Lewis acids - cascade cyclization - bicyclic - natural products synthesis

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