Total synthesis of the post-translationally modified polyazole peptide antibiotic goadsporin

Dexter, Hannah L. and Williams, Huw E.L. and Lewis, William and Moody, Christopher J. (2017) Total synthesis of the post-translationally modified polyazole peptide antibiotic goadsporin. Angewandte Chemie International Edition, 56 (11). pp. 3069-3073. ISSN 1521-3773

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Abstract

The structurally unique polyazole antibiotic goadsporin contains six heteroaromatic oxazole and thiazole rings integrated into a linear array of amino acids that also contains two dehydroalanine residues. An efficient total synthesis of goadsporin is reported in which the key steps are the use of rhodium(II)-catalyzed reactions of diazocarbonyl compounds to generate the four oxazole rings, which demonstrates the power of rhodium carbene chemistry in organic chemical synthesis.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: H. L. Dexter, H. E. L. Williams, W. Lewis, C. J. Moody, Angew. Chem. Int. Ed. 2017, 56, 3069, which has been published in final form at http://dx.doi.org/10.1002/anie.201612103. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Keywords: antibiotics; diazo compounds; heterocycles; peptides; total synthesis
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1002/anie.201612103
Depositing User: Lewis, William
Date Deposited: 27 Sep 2017 11:01
Last Modified: 14 Oct 2017 08:43
URI: http://eprints.nottingham.ac.uk/id/eprint/46635

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