Synlett 2021; 32(18): 1796-1815
DOI: 10.1055/a-1472-4594
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Pivotal Reactions in the Creation of the Polycyclic Skeleton of Cryptotrione

Zhuliang Zhong
b   Department of Chemistry, and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. of China
,
Mao-Yun Lyu
b   Department of Chemistry, and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. of China
,
Hao-Ran Ma
a   School of Science and Engineering, The Chinese University of Hong Kong (Shenzhen), Longgang District, Shenzhen, P. R. of China
,
Henry N. C. Wong
a   School of Science and Engineering, The Chinese University of Hong Kong (Shenzhen), Longgang District, Shenzhen, P. R. of China
b   Department of Chemistry, and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. of China
,
a   School of Science and Engineering, The Chinese University of Hong Kong (Shenzhen), Longgang District, Shenzhen, P. R. of China
b   Department of Chemistry, and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P. R. of China
› Author Affiliations
This work was supported by grants from the National Natural Science Foundation of China (NSFC) (21971219, 21672181), the Research Grants Council (RGC), University Grants Committee (Hong Kong) in the form of the General Research Fund (GRF) (CUHK14304819, CUHK14309216, CUHK14303815 and 403012), the Innovation and Technology Commission - Hong Kong in the form of a subsidy to the State Key Laboratory of Synthetic Chemistry, the Impact Postdoctoral Fellow Scheme, direct grants from the Chinese University of Hong Kong (CUHK), an open grant to CUHK-Shenzhen from the State Key Laboratory of Synthetic Chemistry, and the University Development Fund Grants from The Chinese University of Hong Kong, Shenzhen.


Dedicated to the memory of Professor Shang-Wai Tam, who passed away January 1, 2021

Abstract

Three pivotal reactions, namely, enyne cycloisomerization, polyene cyclization, and quinone methide formation, are applied to synthesize the complex polycyclic skeleton of cryptotrione. This review summarizes the most prominent applications of these three reactions to the total syntheses of natural products, covering results published in the literature between 2011 and 2020.

1 Introduction

2 Three Pivotal Reactions Applied to Create the Polycyclic Framework of Cryptotrione

2.1 Enyne Cycloisomerization

2.2 Polyene Cyclization

2.3 Quinone Methide Formation

3 Conclusion



Publication History

Received: 07 March 2021

Accepted after revision: 31 March 2021

Accepted Manuscript online:
31 March 2021

Article published online:
28 April 2021

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