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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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posted on 06.06.2017 by Robert Lee, Martin Lindley, Gareth Pritchard, Marc Kimber
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.

History

School

  • Science

Department

  • Chemistry

Published in

Chemical Communications (London)

Citation

LEE, R.J. ...et al., 2017. A biosynthetically inspired route to substituted furans using the Appel reaction: total synthesis of the furan fatty acid F5. Chemical Communications, 53 (47), pp. 6327-6330.

Publisher

© Royal Society of Chemistry

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Acceptance date

12/05/2017

Publication date

2017

Notes

This paper was published in the journal Chemical Communications and the definitive published version is available at http://dx.doi.org/10.1039/C7CC03229C.

ISSN

0009-241X

Language

en

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