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A general convergent strategy for the synthesis of tetra-substituted furan fatty acids (FuFAs)

journal contribution
posted on 28.05.2020 by Yamin Wang, Gareth Pritchard, Marc Kimber
Using a palladium catalyzed - acid mediated isomerization sequence, tetrasubstituted furans suitable for furan fatty acid (FuFA) total synthesis can be effectively constructed in high yield. This convergent approach installs the essential carbon side chains at the α1- and α2 -positions, the β1-methyl group, and importantly, an electron withdrawing group at the β2-position tempering the reactivity of the electron rich furan in the FuFAs. When this EWG is an ester, it was conveniently transformed into the required β1-methyl group in three high yielding synthetic steps. Using this approach, the total synthesis of 11D5 and 11D3 was accomplished in 7-steps from commercially available starting materials in overall yields of 52 % and 48 %, respectively. Furthermore, this methodology also provided an efficient synthetic route to the decarboxy analogues of both 11D5 and 11D3.

Funding

Loughborough University

History

School

  • Science

Department

  • Chemistry

Published in

European Journal of Organic Chemistry

Volume

2020

Issue

19

Pages

2914 - 2922

Publisher

Wiley

Version

AM (Accepted Manuscript)

Rights holder

© WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

Publisher statement

This is the peer reviewed version of the following article: WANG, Y., PRITCHARD, G.J. and KIMBER, M.C., 2020. A general convergent strategy for the synthesis of tetra‐substituted furan fatty acids (FuFAs). European Journal of Organic Chemistry, 2020 (19), pp.2914-2922, which has been published in final form at https://doi.org/10.1002/ejoc.202000234. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.

Publication date

2020-03-20

Copyright date

2020

ISSN

1434-193X

eISSN

1099-0690

Language

en

Depositor

Dr Marc Kimber. Deposit date: 28 May 2020

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