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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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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
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author Boehlich, G. Jacob
de Vries, Jessica
Geismar, Olivia
Gudzuhn, Mirja
Streit, Wolfgang R.
Wicha, Sebastian G.
Schützenmeister, Nina
author_facet Boehlich, G. Jacob
de Vries, Jessica
Geismar, Olivia
Gudzuhn, Mirja
Streit, Wolfgang R.
Wicha, Sebastian G.
Schützenmeister, Nina
author_sort Boehlich, G. Jacob
collection PubMed
description 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.
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spelling pubmed-74972752020-09-25 Total Synthesis of Anti‐MRSA Active Diorcinols and Analogues Boehlich, G. Jacob de Vries, Jessica Geismar, Olivia Gudzuhn, Mirja Streit, Wolfgang R. Wicha, Sebastian G. Schützenmeister, Nina Chemistry Communications 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. John Wiley and Sons Inc. 2020-07-01 2020-08-06 /pmc/articles/PMC7497275/ /pubmed/32510795 http://dx.doi.org/10.1002/chem.202002442 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Boehlich, G. Jacob
de Vries, Jessica
Geismar, Olivia
Gudzuhn, Mirja
Streit, Wolfgang R.
Wicha, Sebastian G.
Schützenmeister, Nina
Total Synthesis of Anti‐MRSA Active Diorcinols and Analogues
title Total Synthesis of Anti‐MRSA Active Diorcinols and Analogues
title_full Total Synthesis of Anti‐MRSA Active Diorcinols and Analogues
title_fullStr Total Synthesis of Anti‐MRSA Active Diorcinols and Analogues
title_full_unstemmed Total Synthesis of Anti‐MRSA Active Diorcinols and Analogues
title_short Total Synthesis of Anti‐MRSA Active Diorcinols and Analogues
title_sort total synthesis of anti‐mrsa active diorcinols and analogues
topic Communications
url 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
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