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Type: Artigo
Title: Diastereoselective Synthesis Of Biologically Active Cyclopenta[b]indoles
Author: Santos
Marilia S.; Fernandes
Daniara C.; Rodrigues
Manoel T.
Jr.; Regiani
Thais; Andricopulo
Adriano D.; Ruiz
Ana Lucia T. G.; Vendramini-Costa
Debora B.; de Carvalho
Joao E.; Eberlin
Marcos N.; Coelho
Abstract: The cyclopenta[b]indole motif is present in several natural and synthetic biologically active compounds, being directly responsible for the biological effects some of them present. We described herein a three step sequence for the synthesis of cyclopenta[b]indoles with a great structural diversity. The method is based on an oxidative Michael addition of suitable indoles on the double bond of Morita-Baylis-Hillman adducts mediated by a hypervalent iodine reagent (IBX) to form beta-ketoesters, which were chemoselectively reduced with NaBH4 in THE to give the corresponding beta-hydroxyesters. The diastereoisomeric mixture was then treated with a catalytic amount of triflic acid (20 mol %) to give cyclopenta[b]indoles with overall yields ranging from 8 to 73% (for 2 steps). The acid-catalyzed cyclization step gave the required heterocycles via an intramolecular Friedel Crafts reaction, with high diastereoselectivity, where only the trans product was observed. A mechanistic study monitored by ESI-(+)-MS was also conducted to collect evidence about the mechanism of this reaction. The new molecules herein synthesized were also evaluated against a panel of human cancer cells demonstrating a promising antiturnoral profile.
Editor: Amer Chemical Soc
Citation: Journal Of Organic Chemistry. Amer Chemical Soc, v. 81, p. 6626 - 6639, 2016.
Rights: fechado
Identifier DOI: 10.1021/acs.joc.6b01270
Date Issue: 2016
Appears in Collections:Unicamp - Artigos e Outros Documentos

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