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Total synthesis of the tetrasubstituted furan fatty acid metabolite CeDFP via Au-catalyzed intermolecular alkyne hydroarylation
journal contribution
posted on 2019-07-02, 13:37 authored by Yamin Wang, Gareth PritchardGareth Pritchard, Marc KimberMarc KimberThe 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 LettersVolume
21Issue
12Pages
4892 - 4895Citation
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 SocietyVersion
- 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
2019-06-12Publication date
2019-06-12ISSN
1523-7060eISSN
1523-7052Publisher version
Language
- en