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A biosynthetically inspired route to substituted furans using the Appel reaction: total synthesis of the furan fatty acid F5

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Abstract

Appel reaction conditions have been harnessed to affect a mild biosynthetically inspired dehydration of endoperoxides to deliver multi-substituted electron rich furans. Unlike traditional dehydrative procedures, this method is metal and acid free, and can be achieved under redox neutral conditions. It is general for a range of aryl and alkyl substituted endoperoxides, and is functional group tolerant. Furthermore, this procedure has been used to deliver an effective total synthesis of the furan fatty acid (FFA) F5.

Graphical abstract: A biosynthetically inspired route to substituted furans using the Appel reaction: total synthesis of the furan fatty acid F5

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Publication details

The article was received on 26 Apr 2017, accepted on 12 May 2017 and first published on 19 May 2017


Article type: Communication
DOI: 10.1039/C7CC03229C
Citation: Chem. Commun., 2017, Advance Article
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    A biosynthetically inspired route to substituted furans using the Appel reaction: total synthesis of the furan fatty acid F5

    R. J. Lee, M. R. Lindley, G. J. Pritchard and M. C. Kimber, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC03229C

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