A rapid synthesis of 4-oxazolidinones: total synthesis of synoxazolidinones A and B.
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.
Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh NC 27695 (USA) http://www.ncsu.edu/chemistry/jgp.
Nataliia V
NV
Shymanska
Il Hwan
IH
An
Joshua G
JG
Pierce
D040981:Acinetobacter baumannii / Q000187:drug effects; D000215:Acylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D003500:Cyclization; D019791:Guanidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007097:Imines / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D007097:Imines; D023303:Oxazolidinones; C555088:synoxazolidinone A; C555089:synoxazolidinone B; D019791:Guanidine
antimicrobial agents; heterocycles; natural products; stereoselectivity; total synthesis