6-Azido hyacinthacine A(2) gives a straightforward access to the first multivalent pyrrolizidine architectures

Year: 2014

Authors: D’Adamio G., Parmeggiani C., Goti A., Moreno-Vargas A. J., Moreno-Clavijo E., Robina I., Cardona F.

Autors Affiliation: Univ Florence, Dipartimento Chim Ugo Schiff, I-50019 Sesto Fiorentino, FI, Italy; European Lab Non Linear Spect LENS, I-50019 Sesto Fiorentino, FI, Italy; UOS Sesto Fiorentino, CNR INO, I-50019 Sesto Fiorentino, FI, Italy; Univ Seville, Fac Quim, Dept Quim Organ, E-41012 Seville, Spain

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.

Journal/Review: ORGANIC & BIOMOLECULAR CHEMISTRY

Volume: 12 (32)      Pages from: 6250  to: 6266

More Information: We thank MIUR-Italy (PRIN 2008, 200824M2HX, and PRIN 2010-2011, 2010L9SH3 K 006) and Ente Cassa di Risparmio di Firenze (CRF, 2009/3141) for financial support. The research leading to these results has received funding from the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013)/ERC grant agreement no. [291349] on photonic micro robotics. We thank Ministerio de Economia y Competitividad (CTQ2012-31247) of Spain, Junta de Andalucia (FQM 345) and European Community FP7 program (HEALTH-F2-2011-256986-project acronym PANACREAS) for financial support. We also thank Mr Simone Pisano for preliminary experiments.
KeyWords: Iminosugar Click Clusters; Glycosidase Inhibition; Pharmacological Chaperones; 1,3-dipolar Cycloadditions; Chemistry; Ligands; 7-deoxycasuarine; Reactivity; Dendrimers; Casuarine
DOI: 10.1039/c4ob01117a

Citations: 25
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