Synlett 2018; 29(12): 1552-1571
DOI: 10.1055/s-0037-1610126
account
© Georg Thieme Verlag Stuttgart · New York

Diversity-Oriented Synthesis of Natural Products via Gold-Catalyzed Cascade Reactions

Yueqing Gu
a   State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China   Email: gongjx@pku.edu.cn
,
Ceheng Tan
a   State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China   Email: gongjx@pku.edu.cn
,
Jianxian Gong*
a   State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China   Email: gongjx@pku.edu.cn
,
Zhen Yang  *
a   State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China   Email: gongjx@pku.edu.cn
b   Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering, and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, P. R. of China   Email: zyang@pku.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 10 March 2018

Accepted after revision: 05 April 2018

Publication Date:
16 May 2018 (online)


Abstract

This account describes our group’s latest research in the field of diversity-oriented synthesis of natural products via gold-catalyzed cascade reactions. We present two general strategies based on gold-catalyzed cycloisomerization: a gold-catalyzed cascade reaction of 1,7-diynes and a pinacol-terminated gold-catalyzed cascade reaction. We highlight our development of synthetic methods for the construction of biologically active natural products by using these two strategies.

1 Introduction

2 Gold-Catalyzed Cascade Reactions of 1,7-Diynes

2.1 Collective Synthesis of C15 Oxygenated Drimane-Type Sesquiterpenoids

2.2 Synthesis of Left-Wing Fragment of Azadirachtin I

2.3 Collective Synthesis of Cladiellins

3 Pinacol-Terminated Gold-Catalyzed Cascade Reaction

3.1 Asymmetric Formal Total Synthesis of (+)-Cortistatins

3.2 Total Synthesis of Orientalol F

3.3 Asymmetric Total Synthesis of (–)-Farnesiferol C

4 Summary and Outlook