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A Rapid Synthesis of 4‐Oxazolidinones: Total Synthesis of Synoxazolidinones A and B
Author(s) -
Shymanska Nataliia V.,
An Il Hwan,
Pierce Joshua G.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201402310
Subject(s) - total synthesis , chemistry , natural product , antimicrobial , substituent , acylation , imine , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
A five‐step total synthesis of the marine natural product synoxazolidinone A was achieved through a diastereoselective imine acylation/cyclization cascade. Synoxazolidinone B and a series of analogues were also prepared to explore the potential of these 4‐oxazolidinone natural products as antimicrobial agents. These studies confirmed the importance of the chlorine substituent for antimicrobial activity and revealed simplified dichloro derivatives that are equally potent against several bacterial strains.