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Synlett 2019; 30(06): 642-646
DOI: 10.1055/s-0037-1611943
DOI: 10.1055/s-0037-1611943
synpacts
Alkyne-Forming Furan Fragmentation: A General Method to Convert Furans into Alkynoic Acids
Financial support was provided by the ‘Thousand Youth Talents Plan’, the Strategic Priority Research Program of the Chinese Academy of Sciences (Grant No. XDB20000000), the ‘Shanghai Rising-Star Plan’ (Grant No. 17QA1405100), CAS Key Laboratory of Synthetic Chemistry of Natural Substances, and Shanghai Institute of Organic Chemistry.Further Information
Publication History
Received: 24 November 2018
Accepted after revision: 06 December 2018
Publication Date:
08 January 2019 (online)
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
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For selected examples and reviews, see:
C2-Phenyl furans may undergo O-neophyl rearrangement to afford γ-ketoesters, see: