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Total Synthesis of Anti‐MRSA Active Diorcinols and Analogues

Diorcinols and related prenylated diaryl ethers were reported to exhibit activity against methicillin‐resistant clinical isolates of Staphylococcus aureus (MRSA). Within these lines, we report the first total synthesis of diorcinol D, I, J, the proposed structure of verticilatin and recently isolate...

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Detalles Bibliográficos
Autores principales: Boehlich, G. Jacob, de Vries, Jessica, Geismar, Olivia, Gudzuhn, Mirja, Streit, Wolfgang R., Wicha, Sebastian G., Schützenmeister, Nina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497275/
https://www.ncbi.nlm.nih.gov/pubmed/32510795
http://dx.doi.org/10.1002/chem.202002442
Descripción
Sumario:Diorcinols and related prenylated diaryl ethers were reported to exhibit activity against methicillin‐resistant clinical isolates of Staphylococcus aureus (MRSA). Within these lines, we report the first total synthesis of diorcinol D, I, J, the proposed structure of verticilatin and recently isolated antibacterial diaryl ether by using an efficient and highly divergent synthetic strategy. These total syntheses furnish the diaryl ethers in only five to seven steps employing a Pd‐catalyzed diaryl ether coupling as the key step. The total synthesis led to the structural revision of the natural product verticilatin, which has been isolated from a plant pathogenic fungus. Furthermore, these structures were tested in order to determine their antibacterial activities against different MRSA strains as well as further Gram‐positive and ‐negative bacteria.