Asymmetric synthesis of oxazolidine nucleosides and related chemistry.
Asymmetric synthesis of N-substituted oxazolidinyl nucleosides has been accomplished from L-isoserine, trans- and cis-Oxazolidine intermediates (4 and 5) were stereoselectively constructed from N-protected L-isoserine with a menthoxycarbonyl group by the condensation with benzoyloxy acetaldehyde dimethyl acetal in a ratio of 3.9 to 1 in favor of trans-isomer 4. The major isomer 4 was converted to enantiomerically pure beta- and alpha-N-L-menthoxycarbonyl oxazolidinyl thymine nucleosides 11 and 12 in 6 steps.
Department of Medicinal Chemistry, College of Pharmacy, University of Georgia, Athens 30602, USA.
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D000998:Antiviral Agents / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis*; D010080:Oxazoles / Q000138:chemical synthesis*; D012694:Serine / Q000031:analogs & derivatives / Q000737:chemistry; D013941:Thymine / Q000031:analogs & derivatives
D000998:Antiviral Agents; D009705:Nucleosides; D010080:Oxazoles; D012694:Serine; C072421:isoserine; D013941:Thymine