A practical synthetic scheme was developed to prepare both the cis- and trans-fused stereoisomers of N-Boc-L-octahydroindole-2-carboxylic acid (L-Oic) methyl ester. Key event of the synthetic sequence was the ring-closing metathesis of a suitable diallylated proline derivative. This is the first reported practical synthesis of the trans-fused isomer. Functionalization of the octahydroindole nucleus by electrochemical oxidation followed by acid-catalysed allylation paved the way for the preparation of reverse-turn dipeptide mimics.
|Titolo:||Practical stereoselective synthesis of conformationally constrained unnatural proline-based amino acids and peptidomimetics|
|Parole Chiave:||Octahydroindole ring; Peptidomimetics; Ring-closing metathesis; Unnatural amino acids|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2001|
|Digital Object Identifier (DOI):||10.1016/S0040-4020(01)00538-5|
|Appare nelle tipologie:||01 - Articolo su periodico|