Premium
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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201402310
Subject(s) - total synthesis , antimicrobial , natural product , substituent , acylation , chemistry , imine , combinatorial chemistry , stereochemistry , chlorine , 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.