Dihydropyridine        C-glycoconjugates by organocatalytic Hantzsch cyclocondensation. Stereoselective synthesis of α-threofuranose C-nucleoside enantiomers

Diogo R. B. Ducatti; Alessandro Massi; Miguel D. Noseda; Maria Eugênia R. Duarte; Alessandro Dondoni

doi:10.1039/B900422J

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DihydropyridineC-glycoconjugates by organocatalytic Hantzsch cyclocondensation. Stereoselective synthesis of α-threofuranoseC-nucleoside enantiomers†

Diogo R. B. Ducatti,^ba Alessandro Massi,*^a Miguel D. Noseda,^b Maria Eugênia R. Duarte^b and Alessandro Dondoni*^a

Author affiliations

* Corresponding authors

^a Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, Italy
E-mail: adn@unife.it, msslsn@unife.it

^b Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, Centro Politécnico, CEP 81–531–990, Curitiba, Brazil

Abstract

The Hantzsch reaction of C-glycosyl aldehyde/enamino ester/β-ketoester systems under L-proline catalysis to give dihydropyridineC-glycoconjugates is reported. Asymmetric cyclocondensations of differentially substituted enamine and β-dicarbonyl components with formyl α-L-C-threofuranoside and with the α-D-isomer were also carried out. Each reaction occurred with high yet opposite stereoselectivity (de >95%) so that the pair of α-threofuranose C-nucleoside enantiomers was prepared.

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Supplementary files

¹H and ¹³C NMR spectra of compounds 11a–11e and 13, and ¹H NMR spectrum of epi-11a PDF (5214K)

Article information

DOI: https://doi.org/10.1039/B900422J
Article type: Paper
Submitted: 09 Jan 2009
Accepted: 24 Feb 2009
First published: 24 Mar 2009

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Org. Biomol. Chem., 2009,7, 1980-1986

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Dihydropyridine C-glycoconjugates by organocatalytic Hantzsch cyclocondensation. Stereoselective synthesis of α-threofuranose C-nucleoside enantiomers

D. R. B. Ducatti, A. Massi, M. D. Noseda, M. E. R. Duarte and A. Dondoni, Org. Biomol. Chem., 2009, 7, 1980 DOI: 10.1039/B900422J

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Organic & Biomolecular Chemistry