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

Yueqing Gu; Ceheng Tan; Jianxian Gong; Zhen Yang

doi:10.1055/s-0037-1610126

Synlett, Table of Contents

Synlett 2018; 29(12): 1552-1571
DOI: 10.1055/s-0037-1610126

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

Yueqing Gu

^aState 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

^aState 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*

^aState 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 *

^aState 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

^bKey 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

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Abstract

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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

Key words

gold catalysis - natural products - cascade reaction - total synthesis

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References

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