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

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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