(Chemical Equation Presented) 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.
|Titolo:||An efficient route to all stereoisomeric enantiopure 6-amino-3-alkyl-3-azabicyclo[3.2.1]octane-6-carboxylic acids|
|Autori interni:||CLERICI, FRANCESCA|
GELMI, MARIA LUISA
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2007|
|Digital Object Identifier (DOI):||10.1021/jo7019702|
|Appare nelle tipologie:||01 - Articolo su periodico|