Issue 32, 2014

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
30 May 2014
Accepted
18 Jun 2014
First published
24 Jun 2014

Org. Biomol. Chem., 2014,12, 6250-6266

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 and F. Cardona, Org. Biomol. Chem., 2014, 12, 6250 DOI: 10.1039/C4OB01117A

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