Dihydropyridine C-glycoconjugates by organocatalytic Hantzsch cyclocondensation. Stereoselective synthesis of alpha-threofuranose C-nucleoside enantiomers.
The Hantzsch reaction of C-glycosyl aldehyde/enamino ester/beta-ketoester systems under l-proline catalysis to give dihydropyridine C-glycoconjugates is reported. Asymmetric cyclocondensations of differentially substituted enamine and beta-dicarbonyl components with formyl alpha-L-C-threofuranoside and with the alpha-D-isomer were also carried out. Each reaction occurred with high yet opposite stereoselectivity (de >95%) so that the pair of alpha-threofuranose C-nucleoside enantiomers was prepared.
Ducatti
Diogo R B
DR
Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, Centro Politécnico, CEP 81-531-990, PO Box 19046, Curitiba, Brazil.
Massi
Alessandro
A
Noseda
Miguel D
MD
Duarte
Maria Eugênia R
ME
Dondoni
Alessandro
A
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004095:Dihydropyridines / Q000737:chemistry*; D006001:Glycoconjugates / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis*; D011134:Polysaccharides / Q000737:chemistry; D012624:Seaweed / Q000737:chemistry; D013237:Stereoisomerism; D013780:Tetroses / Q000737:chemistry*
D000447:Aldehydes; D004095:Dihydropyridines; D006001:Glycoconjugates; D009705:Nucleosides; D011134:Polysaccharides; D013780:Tetroses; C038806:1,4-dihydropyridine; C073321:erythrose