Recent Advances in the Total Synthesis of Prenylflavonoid and Related Diels–Alder Natural Products

Jianguang Han; Alexander X. Jones; Xiaoguang Lei

doi:10.1055/s-0034-1378696

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(11): 1519-1533
DOI: 10.1055/s-0034-1378696

review

Recent Advances in the Total Synthesis of Prenylflavonoid and Related Diels–Alder Natural Products

Jianguang Han

^aSchool of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China

,

Alexander X. Jones

^bBeijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology, College of Chemistry and Molecular Engineering, Synthetic and Functional Biomolecules Center, and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, P. R. of China

,

Xiaoguang Lei*

^bBeijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology, College of Chemistry and Molecular Engineering, Synthetic and Functional Biomolecules Center, and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, P. R. of China

^cNational Institute of Biological Sciences (NIBS), Beijing 102206, P. R. of China eMail: xglei@pku.edu.cn

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Abstract

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Abstract

This review summarizes the application of different strategies for the key Diels–Alder cycloaddition in prenylflavonoid and related Diels–Alder natural products synthesis, highlighting the application of novel methodologies and innovative strategies in the synthesis of these natural products and their analogues.

1 Introduction

2 Classical Conditions for the Diels–Alder Cycloaddition

2.1 Thermal Promotion

2.2 High-Pressure Promotion

2.3 Brønsted Acid Catalysis

3 Modern Approaches to the Diels–Alder Cycloaddition

3.1 Electron-Transfer Initiation

3.2 Silver-Nanoparticle Catalysis

3.3 Chiral-Boron-Complex Promotion

4 Conclusion

Key words

prenylflavonoids - total synthesis - Diels–Alder cycloaddition - biomimetic synthesis - asymmetric synthesis

Volltext

Referenzen

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