title: 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.
authors.affiliation: Dipartimento di Chimica "Ugo Schiff", Università di Firenze, Via della Lastruccia 3-13, 50019 Sesto Fiorentino (FI), Italy. francesca.cardona@unifi.it andrea.goti@unifi.it.
authors.forename: Giampiero
authors.initials: G
authors.lastname: D'Adamio
authors.forename: Camilla
authors.initials: C
authors.lastname: Parmeggiani
authors.forename: Andrea
authors.initials: A
authors.lastname: Goti
authors.forename: Antonio J
authors.initials: AJ
authors.lastname: Moreno-Vargas
authors.forename: Elena
authors.initials: E
authors.lastname: Moreno-Clavijo
authors.forename: Inmaculada
authors.initials: I
authors.lastname: Robina
authors.forename: Francesca
authors.initials: F
authors.lastname: Cardona
mesh_terms: D061565:Cycloaddition Reaction; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D012441:Saccharomyces cerevisiae / Q000201:enzymology
chemical_list: C000597370:6-azido hyacinthacine A2; D004791:Enzyme Inhibitors; D011758:Pyrroles; D011763:Pyrrolizidine Alkaloids; C500284:hyacinthacine A2; D006026:Glycoside Hydrolases