The synthesis of the first multivalent pyrrolizidine iminosugars is reported. The key azido intermediates 4 and 31 were prepared after suitable synthetic elaboration of the cycloadduct obtained from 1,3-dipolar cycloaddition of D-arabinose derived nitrone to dimethylacrylamide. The key step of the strategy was the stereoselective installation of an azido moiety at C-6 of the pyrrolizidine skeleton. The click reaction with different monovalent and dendrimeric alkyne scaffolds allowed the preparation of a library of new mono and multivalent pyrrolizidine compounds that were preliminarily assayed as glycosidase inhibitors towards a panel of commercially available glycosyl hydrolases.

6-Azido hyacinthacine A2 gives a straightforward access to the first multivalent pyrrolizidine architectures / G. D’Adamio; C. Parmeggiani; A. Goti; A. J. Moreno-Vargas; E. Moreno-Clavijo; I. Robina; F. Cardona. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - STAMPA. - 12:(2014), pp. 6250-6266. [10.1039/c4ob01117a]

6-Azido hyacinthacine A2 gives a straightforward access to the first multivalent pyrrolizidine architectures

D'ADAMIO, GIAMPIERO;PARMEGGIANI, CAMILLA;GOTI, ANDREA;CARDONA, FRANCESCA
2014

Abstract

The synthesis of the first multivalent pyrrolizidine iminosugars is reported. The key azido intermediates 4 and 31 were prepared after suitable synthetic elaboration of the cycloadduct obtained from 1,3-dipolar cycloaddition of D-arabinose derived nitrone to dimethylacrylamide. The key step of the strategy was the stereoselective installation of an azido moiety at C-6 of the pyrrolizidine skeleton. The click reaction with different monovalent and dendrimeric alkyne scaffolds allowed the preparation of a library of new mono and multivalent pyrrolizidine compounds that were preliminarily assayed as glycosidase inhibitors towards a panel of commercially available glycosyl hydrolases.
2014
12
6250
6266
G. D’Adamio; C. Parmeggiani; A. Goti; A. J. Moreno-Vargas; E. Moreno-Clavijo; I. Robina; F. Cardona
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/910330
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