A Lewis acid-catalysed diastereoselective [4 + 2] cycloaddition of vinylindoles and methyl 2-acetamidoacrylate, leading to methyl 3-acetamido-1,2,3,4-tetrahydrocarbazole-3-carboxylate derivatives, is described. Treatment of the obtained cycloadducts under hydrolytic conditions results in the preparation of a small library of compounds bearing the free amino acid function at C-3 and pertaining to the class of constrained tryptophan analogues.
Synthesis of constrained analogues of tryptophan / E. Rossi, V. Pirovano, M. Negrato, G. Abbiati, M. Dell’Acqua. - In: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1860-5397. - 11(2015 Oct 27), pp. 1997-2006.
Titolo: | Synthesis of constrained analogues of tryptophan |
Autori: | ROSSI, ELISABETTA (Primo) PIROVANO, VALENTINA (Secondo) ABBIATI, GIORGIO (Penultimo) DELL'ACQUA, MONICA (Ultimo) |
Parole Chiave: | constrained tryptophans; Diels–Alder; indoles; tetrahydrocarbazoles; unnatural amino acids |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 27-ott-2015 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.3762/bjoc.11.216 |
Appare nelle tipologie: | 01 - Articolo su periodico |
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