Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration

The reaction of 3-substituted indoles with dehydroalanine (Dha) derivatives under Lewis acid-mediated conditions has been investigated. The formation of 2-substituted tryptophans is proposed to occur through a selective alkylative dearomatization–cyclization followed by C3- to C2-alkyl migration and...

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Autores principales: Mari, Michele, Lucarini, Simone, Bartoccini, Francesca, Piersanti, Giovanni, Spadoni, Gilberto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168769/
https://www.ncbi.nlm.nih.gov/pubmed/25246958
http://dx.doi.org/10.3762/bjoc.10.207
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author Mari, Michele
Lucarini, Simone
Bartoccini, Francesca
Piersanti, Giovanni
Spadoni, Gilberto
author_facet Mari, Michele
Lucarini, Simone
Bartoccini, Francesca
Piersanti, Giovanni
Spadoni, Gilberto
author_sort Mari, Michele
collection PubMed
description The reaction of 3-substituted indoles with dehydroalanine (Dha) derivatives under Lewis acid-mediated conditions has been investigated. The formation of 2-substituted tryptophans is proposed to occur through a selective alkylative dearomatization–cyclization followed by C3- to C2-alkyl migration and rearomatization.
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spelling pubmed-41687692014-09-22 Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration Mari, Michele Lucarini, Simone Bartoccini, Francesca Piersanti, Giovanni Spadoni, Gilberto Beilstein J Org Chem Full Research Paper The reaction of 3-substituted indoles with dehydroalanine (Dha) derivatives under Lewis acid-mediated conditions has been investigated. The formation of 2-substituted tryptophans is proposed to occur through a selective alkylative dearomatization–cyclization followed by C3- to C2-alkyl migration and rearomatization. Beilstein-Institut 2014-08-26 /pmc/articles/PMC4168769/ /pubmed/25246958 http://dx.doi.org/10.3762/bjoc.10.207 Text en Copyright © 2014, Mari 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
Mari, Michele
Lucarini, Simone
Bartoccini, Francesca
Piersanti, Giovanni
Spadoni, Gilberto
Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration
title Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration
title_full Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration
title_fullStr Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration
title_full_unstemmed Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration
title_short Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration
title_sort synthesis of 2-substituted tryptophans via a c3- to c2-alkyl migration
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168769/
https://www.ncbi.nlm.nih.gov/pubmed/25246958
http://dx.doi.org/10.3762/bjoc.10.207
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AT piersantigiovanni synthesisof2substitutedtryptophansviaac3toc2alkylmigration
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