Diastereo- and enantioselective synthesis of 1'-C-branched N,O-nucleosides.
A synthetic approach towards 1'-C-branched N,O-nucleosides is reported, based on 1,3-dipolar cycloaddition of ethoxycarbonylnitrone. The asymmetric version of the process exploits the presence of a chiral auxiliary at the carbon atom of nitrone and leads to beta-D and beta-L nucleosides in good yields.
Saita
M G
MG
Dipartimento Scienze Chimiche, Università di Catania, Catania, Italy. mgsaita@tiscali.it
Chiacchio
U
U
Iannazzo
D
D
Corsaro
A
A
Merino
P
P
Piperno
A
A
Previtera
T
T
Rescifina
A
A
Romeo
G
G
Romeo
R
R
D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D009589:Nitrogen Oxides / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D009589:Nitrogen Oxides; D009705:Nucleosides; C479168:ethoxycarbonylnitrone; C015388:nitrones