An organocatalytic approach to the construction of chiral oxazolidinone rings and application in the synthesis of antibiotic linezolid and its analogues
- PMID: 19006317
- DOI: 10.1021/ol802333n
An organocatalytic approach to the construction of chiral oxazolidinone rings and application in the synthesis of antibiotic linezolid and its analogues
Abstract
An efficient, catalytic asymmetric approach to antibacterial agent linezolid has been developed. The route features organocatalytic, highly enantioselective aldol and Beckman rearrangement reactions. The strategy has also been successfully applied for the preparation of new alpha-substituted analogues with high enantio- and diastereoselectivity.
Similar articles
-
Regioselective and stereospecific synthesis of enantiopure 1,3-oxazolidin-2-ones by intramolecular ring opening of 2-(Boc-aminomethyl)aziridines. Preparation of the antibiotic linezolid.Org Lett. 2008 May 15;10(10):1935-8. doi: 10.1021/ol800443p. Epub 2008 Apr 24. Org Lett. 2008. PMID: 18433140
-
Novel promising linezolid analogues: rational design, synthesis and biological evaluation.Eur J Med Chem. 2013 Nov;69:779-85. doi: 10.1016/j.ejmech.2013.09.035. Epub 2013 Sep 25. Eur J Med Chem. 2013. PMID: 24099997
-
Highly efficient CuI-catalyzed coupling of aryl bromides with oxazolidinones using Buchwald's protocol: a short route to linezolid and toloxatone.Org Lett. 2003 Apr 3;5(7):963-5. doi: 10.1021/ol026902h. Org Lett. 2003. PMID: 12659549
-
Oxazolidinone structure-activity relationships leading to linezolid.Angew Chem Int Ed Engl. 2003 May 9;42(18):2010-23. doi: 10.1002/anie.200200528. Angew Chem Int Ed Engl. 2003. PMID: 12746812 Review.
-
Recent development of potent analogues of oxazolidinone antibacterial agents.Bioorg Med Chem. 2013 Feb 1;21(3):577-91. doi: 10.1016/j.bmc.2012.11.036. Epub 2012 Dec 5. Bioorg Med Chem. 2013. PMID: 23273607 Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Medical