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Title: Total synthesis of micrococcin P1 and thiocillin I enabled by Mo( vi ) catalyst
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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Chemical Science
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1971 to 1975
Sponsoring Org:
National Science Foundation
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