Synthesis of 2'-deoxy-6,3'-methano-cyclo-pyrimidine nucleosides.
The nucleophilic attack of lithiated pyrimidines to a suitably-protected 3-ketosugar, afforded the 3-branched sugar stereospecifically, followed by intramolecular glycosylation to give 6,3'-methano-cyclo-pyrimidine nucleosides. The 2'-deoxygenation was achieved by sequential protection, deprotection and radical reduction.
D007202:Indicators and Reagents; D008094:Lithium; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D011741:Pyrimidine Nucleosides; D013729:Terpenes; D008094:Lithium