title: An efficient route to all stereoisomeric enantiopure 6-amino-3-alkyl-3- azabicyclo[3.2.1]octane-6-carboxylic acids.
abstract: A single-step synthesis on a gram scale of four pure stereoisomers of the 6-amino-3-azabicyclo[3.2.1]octane-6-carboxylic acid was carried out using (R)-1-phenylethylamine to confer chirality. The phenylethyl group, and the p-methoxy group linked to the N-atom, are easily removed by hydrogenolysis to afford the corresponding NH-3 derivatives. A series of N-3-alkyl compounds were prepared by way of a "one-pot" deprotection-alkylation procedure starting from the above key compounds. Their biological activity has been evaluated on the GABA receptor.
authors.affiliation: Istituto di Chimica Organica A. Marchesini, Facoltà di Farmacia, Università di Milano, Via Venezian 21, I-20133 Milano, Italy. marialuisa.gelmi@unimi.it
authors.forename: Maria Luisa
authors.initials: ML
authors.lastname: Gelmi
authors.forename: Cristian
authors.initials: C
authors.lastname: Cattaneo
authors.forename: Sara
authors.initials: S
authors.lastname: Pellegrino
authors.forename: Francesca
authors.initials: F
authors.lastname: Clerici
authors.forename: Marina
authors.initials: M
authors.lastname: Montali
authors.forename: Claudia
authors.initials: C
authors.lastname: Martini
mesh_terms: D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002264:Carboxylic Acids; D014326:Tropanes