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Total Synthesis of the Post‐translationally Modified Polyazole Peptide Antibiotic Goadsporin
Author(s) -
Dexter Hannah L.,
Williams Huw E. L.,
Lewis William,
Moody Christopher J.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201612103
Subject(s) - oxazole , rhodium , thiazole , dehydroalanine , total synthesis , chemistry , carbene , combinatorial chemistry , stereochemistry , peptide , organic chemistry , catalysis , biochemistry
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.