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

Michele Mari; Simone Lucarini; Francesca Bartoccini; Giovanni Piersanti; Gilberto Spadoni

doi:10.3762/bjoc.10.207

Beilstein Journal of Organic Chemistry (Aug 2014)

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

Michele Mari,
Simone Lucarini,
Francesca Bartoccini,
Giovanni Piersanti,
Gilberto Spadoni

Affiliations

Michele Mari: Department of Biomolecular Sciences, University of Urbino “Carlo Bo”, Piazza del Rinascimento 6, 61029 Urbino (PU), Italy
Simone Lucarini: Department of Biomolecular Sciences, University of Urbino “Carlo Bo”, Piazza del Rinascimento 6, 61029 Urbino (PU), Italy
Francesca Bartoccini: Department of Biomolecular Sciences, University of Urbino “Carlo Bo”, Piazza del Rinascimento 6, 61029 Urbino (PU), Italy
Giovanni Piersanti: Department of Biomolecular Sciences, University of Urbino “Carlo Bo”, Piazza del Rinascimento 6, 61029 Urbino (PU), Italy
Gilberto Spadoni: Department of Biomolecular Sciences, University of Urbino “Carlo Bo”, Piazza del Rinascimento 6, 61029 Urbino (PU), Italy

DOI: https://doi.org/10.3762/bjoc.10.207
Journal volume & issue: Vol. 10, no. 1
pp. 1991 – 1998

Abstract

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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.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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