Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline

Starting from (S)-tryptophanol, a formal synthesis of ent-rhyncho-phylline and ent-isorhynchophylline, involving stereoselective cyclocondensation, spirocyclization, and alkylation reactions, and the final adjustment of the oxidation level at the oxindole and piperidine moieties, is reported.

Detalles Bibliográficos
Autores: Amat Tusón, Mercedes, Ramos, Carlos, Pérez Bosch, Maria, Molins i Grau, Elies, Florindo, Pedro, Santos, Maria M. M., Bosch Cartes, Joan
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2013
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/36425
Acceso en línea:https://hdl.handle.net/2445/36425
Access Level:acceso abierto
Palabra clave:Alcaloides
Síntesi asimètrica
Estereoquímica
Alkaloids
Asymmetric synthesis
Stereochemistry
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spelling Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophyllineAmat Tusón, MercedesRamos, CarlosPérez Bosch, MariaMolins i Grau, EliesFlorindo, PedroSantos, Maria M. M.Bosch Cartes, JoanAlcaloidesSíntesi asimètricaEstereoquímicaAlkaloidsAsymmetric synthesisStereochemistryStarting from (S)-tryptophanol, a formal synthesis of ent-rhyncho-phylline and ent-isorhynchophylline, involving stereoselective cyclocondensation, spirocyclization, and alkylation reactions, and the final adjustment of the oxidation level at the oxindole and piperidine moieties, is reported.Royal Society of Chemistry2013info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/36425Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: http://dx.doi.org/10.1039/c2cc38540fChemical Communications, 2013, vol. 49, num. 19, p. 1954-1956http://dx.doi.org/10.1039/c2cc38540f(c) Amat Tusón, Mercedes et al., 2013info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/364252026-05-27T06:46:51Z
dc.title.none.fl_str_mv Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline
title Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline
spellingShingle Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline
Amat Tusón, Mercedes
Alcaloides
Síntesi asimètrica
Estereoquímica
Alkaloids
Asymmetric synthesis
Stereochemistry
title_short Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline
title_full Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline
title_fullStr Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline
title_full_unstemmed Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline
title_sort Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline
dc.creator.none.fl_str_mv Amat Tusón, Mercedes
Ramos, Carlos
Pérez Bosch, Maria
Molins i Grau, Elies
Florindo, Pedro
Santos, Maria M. M.
Bosch Cartes, Joan
author Amat Tusón, Mercedes
author_facet Amat Tusón, Mercedes
Ramos, Carlos
Pérez Bosch, Maria
Molins i Grau, Elies
Florindo, Pedro
Santos, Maria M. M.
Bosch Cartes, Joan
author_role author
author2 Ramos, Carlos
Pérez Bosch, Maria
Molins i Grau, Elies
Florindo, Pedro
Santos, Maria M. M.
Bosch Cartes, Joan
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Alcaloides
Síntesi asimètrica
Estereoquímica
Alkaloids
Asymmetric synthesis
Stereochemistry
topic Alcaloides
Síntesi asimètrica
Estereoquímica
Alkaloids
Asymmetric synthesis
Stereochemistry
description Starting from (S)-tryptophanol, a formal synthesis of ent-rhyncho-phylline and ent-isorhynchophylline, involving stereoselective cyclocondensation, spirocyclization, and alkylation reactions, and the final adjustment of the oxidation level at the oxindole and piperidine moieties, is reported.
publishDate 2013
dc.date.none.fl_str_mv 2013
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/2445/36425
url https://hdl.handle.net/2445/36425
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: http://dx.doi.org/10.1039/c2cc38540f
Chemical Communications, 2013, vol. 49, num. 19, p. 1954-1956
http://dx.doi.org/10.1039/c2cc38540f
dc.rights.none.fl_str_mv (c) Amat Tusón, Mercedes et al., 2013
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Amat Tusón, Mercedes et al., 2013
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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
_version_ 1869408986097254400
score 15.300724

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