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Diastereoselective synthesis of homo-N,O-nucleosides |
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| Authors: | Ugo Chiacchio Filippo Genovese Vito Librando Antonio Rescifina Antonio Procopio |
| Institution: | a Dipartimento di Scienze Chimiche, Università di Catania, Viale Andrea Doria 6, 95125 Catania, Italy b Dipartimento Farmaco-Chimico, Università di Messina, Viale SS. Annunziata, 98168 Messina, Italy c Departamento de Quimica Organica, Facultad de Ciencias-ICMA, Universidad de Zaragoza-CSIC, E-50009 Zaragoza, Aragon, Spain |
| Abstract: | A new class of homo-N,O-nucleosides has been designed, based on the 1,3-dipolar cycloaddition of C-substituted nitrones with allyl nucleobases. The N-methyl-C-ethoxycarbonyl nitrone 1, and the C-α-silyloxymethyl-N-methyl nitrone 7 have been exploited: the stereochemical features of the obtained nucleosides are dependent on the nature of the dipole. The results obtained with DFT calculations fully agree with the experimental results and successfully reproduce the experimentally observed reversal of endo/exo selectivity for nitrones 1 and 7. |
| Keywords: | N-methyl-C-ethoxycarbonyl nitrone C-α-silyloxymethyl-N-methyl nitrone Nucleobases |
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