Synthesis of 2-oxazolidinones from beta-lactams: stereospecific total synthesis of (-)-cytoxazone and all of its stereoisomers.
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].
Mishra
Rajesh Kumar
RK
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.
Coates
Cristina M
CM
Revell
Kevin D
KD
Turos
Edward
E
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*
D000900:Anti-Bacterial Agents; D010080:Oxazoles; D047090:beta-Lactams; C117832:cytoxazone