Synlett 2017; 28(12): 1394-1406
DOI: 10.1055/s-0036-1588777
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© Georg Thieme Verlag Stuttgart · New York

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

Guangyan Du, Gaopeng Wang, Wenjing Ma, Qianqian Yang, Wenli Bao, Xuefeng Liang, Lizhi Zhu, Chi-Sing Lee*
  • Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen University Town, Xili, Shenzhen 518055, P. R. of China   Email: lizc@pkusz.edu.cn
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Publication History

Received: 03 February 2017

Accepted after revision: 15 March 2017

Publication Date:
06 April 2017 (eFirst)

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