Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids

A synthetic route for the enantioselective construction of the tetracyclic spiro[indolizidine-1,3'-oxindole] framework present in a large number of oxindole alkaloids, with a cis H-3/H-15 stereochemistry, a functionalized two-carbon substituent at C-15, and an E-ethylidene substituent at C-20,...

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Autores: Yayik, Nihan, Pérez Bosch, Maria, Molins i Grau, Elies, Bosch Cartes, Joan, Amat Tusón, Mercedes
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2021
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/173571
Acceso en línea:https://hdl.handle.net/2445/173571
Access Level:acceso abierto
Palabra clave:Alcaloides
Enantiòmers
Compostos heterocíclics
Síntesi orgànica
Alkaloids
Enantiomers
Heterocyclic compounds
Organic synthesis
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spelling Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] AlkaloidsYayik, NihanPérez Bosch, MariaMolins i Grau, EliesBosch Cartes, JoanAmat Tusón, MercedesAlcaloidesEnantiòmersCompostos heterocíclicsSíntesi orgànicaAlkaloidsEnantiomersHeterocyclic compoundsOrganic synthesisA synthetic route for the enantioselective construction of the tetracyclic spiro[indolizidine-1,3'-oxindole] framework present in a large number of oxindole alkaloids, with a cis H-3/H-15 stereochemistry, a functionalized two-carbon substituent at C-15, and an E-ethylidene substituent at C-20, is reported. The key steps of the synthesis are the generation of the tetracyclic spirooxindole ring system by stereoselective spirocyclization from a tryptophanol-derived oxazolopiperidone lactam, the removal of the hydroxymethyl group, and the stereoselective introduction of the E-ethylidene substituent by acetylation at the -position of the lactam carbonyl, followed by hydride reduction and elimination. Following this route, the 21-oxo derivative of the enantiomer of the alkaloid 7(S)-geissoschizol oxindole has been prepared.MDPI2021info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://hdl.handle.net/2445/173571Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésReproducció del document publicat a: https://doi.org/10.3390/molecules26020428Molecules, 2021, vol. 26, p. 428-442https://doi.org/10.3390/molecules26020428cc-by (c) Yayik, Nihan et al., 2021http://creativecommons.org/licenses/by/3.0/esinfo:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1735712026-05-27T06:46:51Z
dc.title.none.fl_str_mv Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids
title Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids
spellingShingle Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids
Yayik, Nihan
Alcaloides
Enantiòmers
Compostos heterocíclics
Síntesi orgànica
Alkaloids
Enantiomers
Heterocyclic compounds
Organic synthesis
title_short Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids
title_full Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids
title_fullStr Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids
title_full_unstemmed Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids
title_sort Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids
dc.creator.none.fl_str_mv Yayik, Nihan
Pérez Bosch, Maria
Molins i Grau, Elies
Bosch Cartes, Joan
Amat Tusón, Mercedes
author Yayik, Nihan
author_facet Yayik, Nihan
Pérez Bosch, Maria
Molins i Grau, Elies
Bosch Cartes, Joan
Amat Tusón, Mercedes
author_role author
author2 Pérez Bosch, Maria
Molins i Grau, Elies
Bosch Cartes, Joan
Amat Tusón, Mercedes
author2_role author
author
author
author
dc.subject.none.fl_str_mv Alcaloides
Enantiòmers
Compostos heterocíclics
Síntesi orgànica
Alkaloids
Enantiomers
Heterocyclic compounds
Organic synthesis
topic Alcaloides
Enantiòmers
Compostos heterocíclics
Síntesi orgànica
Alkaloids
Enantiomers
Heterocyclic compounds
Organic synthesis
description A synthetic route for the enantioselective construction of the tetracyclic spiro[indolizidine-1,3'-oxindole] framework present in a large number of oxindole alkaloids, with a cis H-3/H-15 stereochemistry, a functionalized two-carbon substituent at C-15, and an E-ethylidene substituent at C-20, is reported. The key steps of the synthesis are the generation of the tetracyclic spirooxindole ring system by stereoselective spirocyclization from a tryptophanol-derived oxazolopiperidone lactam, the removal of the hydroxymethyl group, and the stereoselective introduction of the E-ethylidene substituent by acetylation at the -position of the lactam carbonyl, followed by hydride reduction and elimination. Following this route, the 21-oxo derivative of the enantiomer of the alkaloid 7(S)-geissoschizol oxindole has been prepared.
publishDate 2021
dc.date.none.fl_str_mv 2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/173571
url https://hdl.handle.net/2445/173571
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Reproducció del document publicat a: https://doi.org/10.3390/molecules26020428
Molecules, 2021, vol. 26, p. 428-442
https://doi.org/10.3390/molecules26020428
dc.rights.none.fl_str_mv cc-by (c) Yayik, Nihan et al., 2021
http://creativecommons.org/licenses/by/3.0/es
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by (c) Yayik, Nihan et al., 2021
http://creativecommons.org/licenses/by/3.0/es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia)
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 15,300724

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