Issue 47, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
26 Apr 2017
Accepted
12 May 2017
First published
19 May 2017

Chem. Commun., 2017,53, 6327-6330

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, 53, 6327 DOI: 10.1039/C7CC03229C

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