title: Synthesis of 2-oxazolidinones from beta-lactams: stereospecific total synthesis of (-)-cytoxazone and all of its stereoisomers.
abstract: The synthetic correlation between two different antibiotic frameworks, the beta-lactams and 2-oxazolidinones, is described for the first time. In this approach, 2-oxazolidinones are prepared in stereomerically pure form from 3-hydroxy beta-lactams by a ring-opening-cyclization isomerization process. Application of this methodology to the total synthesis of the cytokine modulator, (-)-cytoxazone, and its three stereoisomers is demonstrated. [reaction: see text].
authors.affiliation: Center for Molecular Diversity in Drug Design, Discovery, and Delivery, Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, Florida 33620, USA.
authors.forename: Rajesh Kumar
authors.initials: RK
authors.lastname: Mishra
authors.forename: Cristina M
authors.initials: CM
authors.lastname: Coates
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Revell
authors.forename: Edward
authors.initials: E
authors.lastname: Turos
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000378:metabolism; D047090:beta-Lactams / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D010080:Oxazoles; D047090:beta-Lactams; C117832:cytoxazone