The first enantioselective synthesis of -D and -L N,O-psiconucleosides is reported. The synthetic approach is based on the asymmetric 1,3-dipolar cycloaddition of the C-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-N-methyl nitrone with ethyl 2-acetyloxyacrylate followed by Vorbruggen nucleosidation, and removal of the chiral auxiliary. Stereochemical assignments are supported by a DFT theoretical study of the cycloaddition reaction.
Enantioselective synthesis of N,O-psiconucleosides
IANNAZZO, Daniela;PIPERNO, Anna;ROMEO, Giovanni
2003-01-01
Abstract
The first enantioselective synthesis of -D and -L N,O-psiconucleosides is reported. The synthetic approach is based on the asymmetric 1,3-dipolar cycloaddition of the C-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-N-methyl nitrone with ethyl 2-acetyloxyacrylate followed by Vorbruggen nucleosidation, and removal of the chiral auxiliary. Stereochemical assignments are supported by a DFT theoretical study of the cycloaddition reaction.File in questo prodotto:
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