Practical stereoselective synthesis of conformationally constrained unnatural proline-based amino acids and peptidomimetics
Articolo
Data di Pubblicazione:
2001
Citazione:
Practical stereoselective synthesis of conformationally constrained unnatural proline-based amino acids and peptidomimetics / L. Belvisi, L. Colombo, M. Colombo, M. Di Giacomo, L. Manzoni, B. Vodopivec, C. Scolastico. - In: TETRAHEDRON. - ISSN 0040-4020. - 57:30(2001), pp. 6463-6473.
Abstract:
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.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Octahydroindole ring; Peptidomimetics; Ring-closing metathesis; Unnatural amino acids
Elenco autori:
L. Belvisi, L. Colombo, M. Colombo, M. Di Giacomo, L. Manzoni, B. Vodopivec, C. Scolastico
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