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

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 rh...

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Bibliographic Details
Main Authors: Dexter, Hannah L., Williams, Huw E.L., Lewis, William, Moody, Christopher J.
Format: Article
Published: Wiley-VCH Verlag 2017
Subjects:
Online Access:https://eprints.nottingham.ac.uk/46635/
Description
Summary: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.