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

Dexter, Hannah L.; Williams, Huw E.L.; Lewis, William; Moody, Christopher J.

Authors

Hannah L. Dexter

Huw E.L. Williams

William Lewis

Christopher J. Moody



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.

Journal Article Type Article
Publication Date Mar 6, 2017
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1521-3773
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 56
Issue 11
Pages 3069-3073
APA6 Citation Dexter, H. L., Williams, H. E., Lewis, W., & Moody, C. J. (2017). Total synthesis of the post-translationally modified polyazole peptide antibiotic goadsporin. Angewandte Chemie International Edition, 56(11), 3069-3073. https://doi.org/10.1002/anie.201612103
DOI https://doi.org/10.1002/anie.201612103
Keywords antibiotics; diazo compounds; heterocycles; peptides; total synthesis
Publisher URL https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201612103
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
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.

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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