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Total Synthesis of Anti‐MRSA Active Diorcinols and Analogues
Author(s) -
Boehlich G. Jacob,
Vries Jessica,
Geismar Olivia,
Gudzuhn Mirja,
Streit Wolfgang R.,
Wicha Sebastian G.,
Schützenmeister Nina
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202002442
Subject(s) - total synthesis , antibacterial activity , staphylococcus aureus , natural product , ether , fungus , chemistry , stereochemistry , bacteria , microbiology and biotechnology , pathogenic bacteria , prenylation , combinatorial chemistry , biology , organic chemistry , botany , enzyme , genetics
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.