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Issue 7, 2019
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Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst

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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.

Graphical abstract: Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst

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Supplementary files

Article information


Submitted
01 Nov 2018
Accepted
03 Dec 2018
First published
03 Dec 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 1971-1975
Article type
Edge Article

Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(VI) catalyst

S. Akasapu, A. B. Hinds, W. C. Powell and M. A. Walczak, Chem. Sci., 2019, 10, 1971
DOI: 10.1039/C8SC04885A

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