Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis

The azocino[4,3-b]indole system, tricyclic substructure of the indole alkaloids apparicine and ervaticine, is efficiently assembled by ring-closing metathesis of 2-allyl-3-(allylaminomethyl)indoles. The metathesis sites are introduced into the indole nucleus by reductive amination of a 3-formyl deri...

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Detalles Bibliográficos
Autores: Bennasar Fèlix, M. Lluïsa, Zulaica Gallego, Ester, Solé Arjó, Daniel, Alonso Serrano, Sandra
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2007
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/160425
Acceso en línea:https://hdl.handle.net/2445/160425
Access Level:acceso abierto
Palabra clave:Alcaloides
Metàtesi (Química)
Síntesi orgànica
Alkaloids
Metathesis (Chemistry)
Organic synthesis
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spelling Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesisBennasar Fèlix, M. LluïsaZulaica Gallego, EsterSolé Arjó, DanielAlonso Serrano, SandraAlcaloidesMetàtesi (Química)Síntesi orgànicaAlkaloidsMetathesis (Chemistry)Organic synthesisThe azocino[4,3-b]indole system, tricyclic substructure of the indole alkaloids apparicine and ervaticine, is efficiently assembled by ring-closing metathesis of 2-allyl-3-(allylaminomethyl)indoles. The metathesis sites are introduced into the indole nucleus by reductive amination of a 3-formyl derivative with allylamine, followed by a-lithiation with subsequent electrophilic trapping with acrolein.Elsevier B.V.2007info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/160425Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: https://doi.org/10.1016/j.tet.2006.11.043Tetrahedron, 2007, vol. 63, num. 4, p. 861-866https://doi.org/10.1016/j.tet.2006.11.043(c) Elsevier B.V., 2007info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1604252026-05-27T06:46:51Z
dc.title.none.fl_str_mv Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis
title Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis
spellingShingle Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis
Bennasar Fèlix, M. Lluïsa
Alcaloides
Metàtesi (Química)
Síntesi orgànica
Alkaloids
Metathesis (Chemistry)
Organic synthesis
title_short Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis
title_full Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis
title_fullStr Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis
title_full_unstemmed Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis
title_sort Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis
dc.creator.none.fl_str_mv Bennasar Fèlix, M. Lluïsa
Zulaica Gallego, Ester
Solé Arjó, Daniel
Alonso Serrano, Sandra
author Bennasar Fèlix, M. Lluïsa
author_facet Bennasar Fèlix, M. Lluïsa
Zulaica Gallego, Ester
Solé Arjó, Daniel
Alonso Serrano, Sandra
author_role author
author2 Zulaica Gallego, Ester
Solé Arjó, Daniel
Alonso Serrano, Sandra
author2_role author
author
author
dc.subject.none.fl_str_mv Alcaloides
Metàtesi (Química)
Síntesi orgànica
Alkaloids
Metathesis (Chemistry)
Organic synthesis
topic Alcaloides
Metàtesi (Química)
Síntesi orgànica
Alkaloids
Metathesis (Chemistry)
Organic synthesis
description The azocino[4,3-b]indole system, tricyclic substructure of the indole alkaloids apparicine and ervaticine, is efficiently assembled by ring-closing metathesis of 2-allyl-3-(allylaminomethyl)indoles. The metathesis sites are introduced into the indole nucleus by reductive amination of a 3-formyl derivative with allylamine, followed by a-lithiation with subsequent electrophilic trapping with acrolein.
publishDate 2007
dc.date.none.fl_str_mv 2007
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/160425
url https://hdl.handle.net/2445/160425
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1016/j.tet.2006.11.043
Tetrahedron, 2007, vol. 63, num. 4, p. 861-866
https://doi.org/10.1016/j.tet.2006.11.043
dc.rights.none.fl_str_mv (c) Elsevier B.V., 2007
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Elsevier B.V., 2007
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier B.V.
publisher.none.fl_str_mv Elsevier B.V.
dc.source.none.fl_str_mv Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301603

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