OL submission revision.pdf (532.04 kB)

Total synthesis of the tetrasubstituted furan fatty acid metabolite CeDFP via Au-catalyzed intermolecular alkyne hydroarylation

Download (532.04 kB)
journal contribution
posted on 02.07.2019, 13:37 by Yamin Wang, Gareth Pritchard, Marc Kimber
The first total synthesis of the tetrasubstituted furan fatty acid (FFA) metabolite 5-[(1 E)-2-carboxyethenyl]-3,4-dimethyl-2-furanpentanoic acid (CeDFP) is reported. CeDFP is a FFA metabolite isolated from shark livers and is related to the known FFA metabolites CMPF and CMPentylF. Key elements of the synthetic route to CeDFP include an iodine-promoted 5- endo- dig cyclization of a 1,2-alkyne diol, a methyllithium-mediated insertion of the C3-methyl group, and a Au(I)-catalyzed intermolecular hydroarylation to introduce the unsaturated ester.

History

School

  • Science

Department

  • Chemistry

Published in

Organic Letters

Volume

21

Issue

12

Pages

4892 - 4895

Citation

WANG, Y., PRITCHARD, G.J. and KIMBER, M.C., 2019. Total synthesis of the tetrasubstituted furan fatty acid metabolite CeDFP via Au-catalyzed intermolecular alkyne hydroarylation. Organic Letters, 21 (12), pp. 4892 - 4895.

Publisher

© American Chemical Society

Version

AM (Accepted Manuscript)

Publisher statement

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.orglett.9b01786.

Acceptance date

12/06/2019

Publication date

2019-06-12

ISSN

1523-7060

eISSN

1523-7052

Language

en

Exports

Logo branding

Keywords

Exports