Alkyne-Forming Furan Fragmentation: A General Method to Convert Furans into Alkynoic Acids

Jiachen Deng; Jinghan Gui

doi:10.1055/s-0037-1611943

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(06): 642-646
DOI: 10.1055/s-0037-1611943

synpacts

Alkyne-Forming Furan Fragmentation: A General Method to Convert Furans into Alkynoic Acids

Jiachen Deng

,

Jinghan Gui *

CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China eMail: guijh@sioc.ac.cn

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Abstract

Alle Artikel dieser Rubrik

In memory of Prof. Wei-Shan Zhou on the occasion of the 95th anniversary of his birth.

Abstract

Furans are readily available and highly reactive heterocycles that serve as versatile four-carbon synthons in organic synthesis. Recently, we discovered that furans, upon oxidation with singlet oxygen, can be transformed into alkynes via dual C–C double-bond cleavage. This Synpacts article presents an overview of the historical context and the development of this furan fragmentation reaction. We also discuss its application in natural product synthesis and a plausible reaction mechanism.

1 Introduction

2 Background of Alkyne-Forming Furan Fragmentation

3 Reaction Development

4 Conclusion

Key words

furans - alkynes - singlet oxygen - fragmentation - cycloaddition - ring strain - natural products

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Referenzen

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