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An Approach to Modify 14-Membered Lactone Macrolide Antibiotic Scaffolds

[Image: see text] A ketolide derivative with (12R)-configuration was obtained via a novel ketene acetal in acidic conditions. The structure of this atypical β-keto ketene acetal intermediate within the macrocyclic system has been determined by NMR and X-ray methods. The use of basic conditions at an...

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Detalles Bibliográficos
Autores principales: Janas, Anna, Pyta, Krystian, Gdaniec, Maria, Przybylski, Piotr
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8902751/
https://www.ncbi.nlm.nih.gov/pubmed/35020381
http://dx.doi.org/10.1021/acs.joc.1c02799
Descripción
Sumario:[Image: see text] A ketolide derivative with (12R)-configuration was obtained via a novel ketene acetal in acidic conditions. The structure of this atypical β-keto ketene acetal intermediate within the macrocyclic system has been determined by NMR and X-ray methods. The use of basic conditions at an elevated temperature yielded new, doubly α,β-unsaturated ketone macrolide derivatives with (4E)-configuration as two conformational isomers of folded-in or folded-out conformations.