Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles

The development of a Lewis acid-catalyzed, intramolecular ring-opening benzannulation of 5-(indolyl)2,3-dihydrofuran acetals is described. The resulting 1-hydroxycarbazole-2-carboxylates are formed in up to 90% yield in 1 h. The dihydrofuran acetals are readily accessed from the reactions of enol et...

Descripción completa

Detalles Bibliográficos
Autores principales: Yuan, Shaoren, Guerra Faura, Gabriel, Areheart, Hailey E., Peulen, Natalie E., France, Stefan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9737012/
https://www.ncbi.nlm.nih.gov/pubmed/36500437
http://dx.doi.org/10.3390/molecules27238344
_version_ 1784847178371432448
author Yuan, Shaoren
Guerra Faura, Gabriel
Areheart, Hailey E.
Peulen, Natalie E.
France, Stefan
author_facet Yuan, Shaoren
Guerra Faura, Gabriel
Areheart, Hailey E.
Peulen, Natalie E.
France, Stefan
author_sort Yuan, Shaoren
collection PubMed
description The development of a Lewis acid-catalyzed, intramolecular ring-opening benzannulation of 5-(indolyl)2,3-dihydrofuran acetals is described. The resulting 1-hydroxycarbazole-2-carboxylates are formed in up to 90% yield in 1 h. The dihydrofuran acetals are readily accessed from the reactions of enol ethers and α-diazo-β-indolyl-β-ketoesters. To highlight the method’s synthetic utility, a formal total synthesis of murrayafoline A, a bioactive carbazole-containing natural product, was undertaken.
format Online
Article
Text
id pubmed-9737012
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-97370122022-12-11 Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles Yuan, Shaoren Guerra Faura, Gabriel Areheart, Hailey E. Peulen, Natalie E. France, Stefan Molecules Article The development of a Lewis acid-catalyzed, intramolecular ring-opening benzannulation of 5-(indolyl)2,3-dihydrofuran acetals is described. The resulting 1-hydroxycarbazole-2-carboxylates are formed in up to 90% yield in 1 h. The dihydrofuran acetals are readily accessed from the reactions of enol ethers and α-diazo-β-indolyl-β-ketoesters. To highlight the method’s synthetic utility, a formal total synthesis of murrayafoline A, a bioactive carbazole-containing natural product, was undertaken. MDPI 2022-11-30 /pmc/articles/PMC9737012/ /pubmed/36500437 http://dx.doi.org/10.3390/molecules27238344 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Yuan, Shaoren
Guerra Faura, Gabriel
Areheart, Hailey E.
Peulen, Natalie E.
France, Stefan
Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles
title Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles
title_full Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles
title_fullStr Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles
title_full_unstemmed Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles
title_short Lewis Acid-Catalyzed 2,3-Dihydrofuran Acetal Ring-Opening Benzannulations toward Functionalized 1-Hydroxycarbazoles
title_sort lewis acid-catalyzed 2,3-dihydrofuran acetal ring-opening benzannulations toward functionalized 1-hydroxycarbazoles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9737012/
https://www.ncbi.nlm.nih.gov/pubmed/36500437
http://dx.doi.org/10.3390/molecules27238344
work_keys_str_mv AT yuanshaoren lewisacidcatalyzed23dihydrofuranacetalringopeningbenzannulationstowardfunctionalized1hydroxycarbazoles
AT guerrafauragabriel lewisacidcatalyzed23dihydrofuranacetalringopeningbenzannulationstowardfunctionalized1hydroxycarbazoles
AT arehearthaileye lewisacidcatalyzed23dihydrofuranacetalringopeningbenzannulationstowardfunctionalized1hydroxycarbazoles
AT peulennataliee lewisacidcatalyzed23dihydrofuranacetalringopeningbenzannulationstowardfunctionalized1hydroxycarbazoles
AT francestefan lewisacidcatalyzed23dihydrofuranacetalringopeningbenzannulationstowardfunctionalized1hydroxycarbazoles

Ejemplares similares