Synthesis of constrained analogues of tryptophan

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 prepara...

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Autores principales: Rossi, Elisabetta, Pirovano, Valentina, Negrato, Marco, Abbiati, Giorgio, Dell’Acqua, Monica
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4661003/
https://www.ncbi.nlm.nih.gov/pubmed/26664620
http://dx.doi.org/10.3762/bjoc.11.216
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author Rossi, Elisabetta
Pirovano, Valentina
Negrato, Marco
Abbiati, Giorgio
Dell’Acqua, Monica
author_facet Rossi, Elisabetta
Pirovano, Valentina
Negrato, Marco
Abbiati, Giorgio
Dell’Acqua, Monica
author_sort Rossi, Elisabetta
collection PubMed
description 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.
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spelling pubmed-46610032015-12-09 Synthesis of constrained analogues of tryptophan Rossi, Elisabetta Pirovano, Valentina Negrato, Marco Abbiati, Giorgio Dell’Acqua, Monica Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2015-10-27 /pmc/articles/PMC4661003/ /pubmed/26664620 http://dx.doi.org/10.3762/bjoc.11.216 Text en Copyright © 2015, Rossi et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Rossi, Elisabetta
Pirovano, Valentina
Negrato, Marco
Abbiati, Giorgio
Dell’Acqua, Monica
Synthesis of constrained analogues of tryptophan
title Synthesis of constrained analogues of tryptophan
title_full Synthesis of constrained analogues of tryptophan
title_fullStr Synthesis of constrained analogues of tryptophan
title_full_unstemmed Synthesis of constrained analogues of tryptophan
title_short Synthesis of constrained analogues of tryptophan
title_sort synthesis of constrained analogues of tryptophan
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4661003/
https://www.ncbi.nlm.nih.gov/pubmed/26664620
http://dx.doi.org/10.3762/bjoc.11.216
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