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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Main Authors:	Michele Mari, Simone Lucarini, Francesca Bartoccini, Giovanni Piersanti, Gilberto Spadoni
Format:	Article
Language:	English
Published:	Beilstein-Institut 2014-08-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	Dehydroalanine Friedel–Crafts alkylation indoles migration tryptophans
Online Access:	https://doi.org/10.3762/bjoc.10.207

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spelling	doaj-0ca4d70d75a54562bc793409b424cb852021-02-02T03:25:54ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-08-011011991199810.3762/bjoc.10.2071860-5397-10-207Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migrationMichele Mari0Simone Lucarini1Francesca Bartoccini2Giovanni Piersanti3Gilberto Spadoni4Department of Biomolecular Sciences, University of Urbino “Carlo Bo”, Piazza del Rinascimento 6, 61029 Urbino (PU), ItalyDepartment of Biomolecular Sciences, University of Urbino “Carlo Bo”, Piazza del Rinascimento 6, 61029 Urbino (PU), ItalyDepartment of Biomolecular Sciences, University of Urbino “Carlo Bo”, Piazza del Rinascimento 6, 61029 Urbino (PU), ItalyDepartment of Biomolecular Sciences, University of Urbino “Carlo Bo”, Piazza del Rinascimento 6, 61029 Urbino (PU), ItalyDepartment of Biomolecular Sciences, University of Urbino “Carlo Bo”, Piazza del Rinascimento 6, 61029 Urbino (PU), ItalyThe 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.https://doi.org/10.3762/bjoc.10.207DehydroalanineFriedel–Crafts alkylationindolesmigrationtryptophans
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Michele Mari Simone Lucarini Francesca Bartoccini Giovanni Piersanti Gilberto Spadoni
spellingShingle	Michele Mari Simone Lucarini Francesca Bartoccini Giovanni Piersanti Gilberto Spadoni Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration Beilstein Journal of Organic Chemistry Dehydroalanine Friedel–Crafts alkylation indoles migration tryptophans
author_facet	Michele Mari Simone Lucarini Francesca Bartoccini Giovanni Piersanti Gilberto Spadoni
author_sort	Michele Mari
title	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_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_sort	synthesis of 2-substituted tryptophans via a c3- to c2-alkyl migration
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2014-08-01
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.
topic	Dehydroalanine Friedel–Crafts alkylation indoles migration tryptophans
url	https://doi.org/10.3762/bjoc.10.207
work_keys_str_mv	AT michelemari synthesisof2substitutedtryptophansviaac3toc2alkylmigration AT simonelucarini synthesisof2substitutedtryptophansviaac3toc2alkylmigration AT francescabartoccini synthesisof2substitutedtryptophansviaac3toc2alkylmigration AT giovannipiersanti synthesisof2substitutedtryptophansviaac3toc2alkylmigration AT gilbertospadoni synthesisof2substitutedtryptophansviaac3toc2alkylmigration
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Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration

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