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Total Synthesis of Micrococcin P1 and Thiocillin I Enabled by Mo(VI) Catalyst

Abstract

Thiopeptides are a class of potent antibiotics with promising therapeutic potential. We developed a novel Mo(VI)-oxide/picolinic acid catalyst for the cyclodehydration of cysteine peptides to form thiazoline heterocycles. With this powerful tool in hand, we completed the total syntheses of two representative thiopeptide antibiotics: micrococcin P1 and thiocillin I. These two concise syntheses (15 steps, longest linear sequence) feature a C-H activation strategy to install the trisubstituted pyridine core and thiazole groups. The synthetic material displays promising antimicrobial properties measured against a series of Gram-positive bacteria.

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Publication details

The article was received on 01 Nov 2018, accepted on 03 Dec 2018 and first published on 03 Dec 2018


Article type: Edge Article
DOI: 10.1039/C8SC04885A
Citation: Chem. Sci., 2019, Accepted Manuscript
  • Open access: Creative Commons BY-NC license
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    Total Synthesis of Micrococcin P1 and Thiocillin I Enabled by Mo(VI) Catalyst

    S. Akasapu, A. Hinds, W. Powell and M. Walczak, Chem. Sci., 2019, Accepted Manuscript , DOI: 10.1039/C8SC04885A

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