Issue 7, 2019

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.

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY-NC license

Chem. Sci., 2019,10, 1971-1975

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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