Common scaffolds for the enantioselective synthesis of marine, plant, and amphibian cis-decahydroquinoline alkaloids

[eng] Chiral amino alcohol derived lactams are a valuable scaffold for the enantioselective synthesis of alkaloids. In the present thesis the potential of this methodology was expanded and to demonstrate the synthetic utility of chiral tricyclic lactams obtainedthe enantioselective total synthesis c...

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Detalles Bibliográficos
Autor: Pinto, Alexandre
Tipo de recurso: tesis doctoral
Estado:Versión publicada
Fecha de publicación:2017
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/118698
Acceso en línea:https://hdl.handle.net/2445/118698
http://hdl.handle.net/10803/457969
Access Level:acceso abierto
Palabra clave:Productes naturals
Catàlisi asimètrica
Síntesi de fàrmacs
Alcaloides
Natural products
Enantioselective catalysis
Drug synthesis
Alkaloids
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spelling Common scaffolds for the enantioselective synthesis of marine, plant, and amphibian cis-decahydroquinoline alkaloidsPinto, AlexandreProductes naturalsCatàlisi asimètricaSíntesi de fàrmacsAlcaloidesNatural productsEnantioselective catalysisDrug synthesisAlkaloids[eng] Chiral amino alcohol derived lactams are a valuable scaffold for the enantioselective synthesis of alkaloids. In the present thesis the potential of this methodology was expanded and to demonstrate the synthetic utility of chiral tricyclic lactams obtainedthe enantioselective total synthesis complex cis-decahydroquinoline alkaloids was carried out. The alkaloids that were targeted for synthesis using the developed methodology were the lepadin alkaloids (marine alkaloids) and tricyclic cis-decahydroquinoline alkaloids such as cermizine B (Lycopodium alkaloids). To accomplish these objectives further studies on the functionalization of the decahydroquinoline system were required in order to install the appropriate substituents and functionalities for the synthesis of each target. During the present PhD thesis it was possible to complete the total synthesis of (+)-gephyrotoxin 287C, (−)-cermizine B, (−)-lepadin B and (+)-lepadin D and the formal total synthesis of (−)-lepadins A and C.Universitat de BarcelonaAmat Tusón, MercedesGriera Farres, RosaUniversitat de Barcelona. Departament de Farmacologia, Toxicologia i Química Terapèutica2017info:eu-repo/semantics/doctoralThesisinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://hdl.handle.net/2445/118698http://hdl.handle.net/10803/457969Tesis Doctorals - Departament - Farmacologia, Toxicologia i Química Terapèuticareponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglés(c) Pinto,, 2017info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1186982026-05-27T06:46:51Z
dc.title.none.fl_str_mv Common scaffolds for the enantioselective synthesis of marine, plant, and amphibian cis-decahydroquinoline alkaloids
title Common scaffolds for the enantioselective synthesis of marine, plant, and amphibian cis-decahydroquinoline alkaloids
spellingShingle Common scaffolds for the enantioselective synthesis of marine, plant, and amphibian cis-decahydroquinoline alkaloids
Pinto, Alexandre
Productes naturals
Catàlisi asimètrica
Síntesi de fàrmacs
Alcaloides
Natural products
Enantioselective catalysis
Drug synthesis
Alkaloids
title_short Common scaffolds for the enantioselective synthesis of marine, plant, and amphibian cis-decahydroquinoline alkaloids
title_full Common scaffolds for the enantioselective synthesis of marine, plant, and amphibian cis-decahydroquinoline alkaloids
title_fullStr Common scaffolds for the enantioselective synthesis of marine, plant, and amphibian cis-decahydroquinoline alkaloids
title_full_unstemmed Common scaffolds for the enantioselective synthesis of marine, plant, and amphibian cis-decahydroquinoline alkaloids
title_sort Common scaffolds for the enantioselective synthesis of marine, plant, and amphibian cis-decahydroquinoline alkaloids
dc.creator.none.fl_str_mv Pinto, Alexandre
author Pinto, Alexandre
author_facet Pinto, Alexandre
author_role author
dc.contributor.none.fl_str_mv Amat Tusón, Mercedes
Griera Farres, Rosa
Universitat de Barcelona. Departament de Farmacologia, Toxicologia i Química Terapèutica
dc.subject.none.fl_str_mv Productes naturals
Catàlisi asimètrica
Síntesi de fàrmacs
Alcaloides
Natural products
Enantioselective catalysis
Drug synthesis
Alkaloids
topic Productes naturals
Catàlisi asimètrica
Síntesi de fàrmacs
Alcaloides
Natural products
Enantioselective catalysis
Drug synthesis
Alkaloids
description [eng] Chiral amino alcohol derived lactams are a valuable scaffold for the enantioselective synthesis of alkaloids. In the present thesis the potential of this methodology was expanded and to demonstrate the synthetic utility of chiral tricyclic lactams obtainedthe enantioselective total synthesis complex cis-decahydroquinoline alkaloids was carried out. The alkaloids that were targeted for synthesis using the developed methodology were the lepadin alkaloids (marine alkaloids) and tricyclic cis-decahydroquinoline alkaloids such as cermizine B (Lycopodium alkaloids). To accomplish these objectives further studies on the functionalization of the decahydroquinoline system were required in order to install the appropriate substituents and functionalities for the synthesis of each target. During the present PhD thesis it was possible to complete the total synthesis of (+)-gephyrotoxin 287C, (−)-cermizine B, (−)-lepadin B and (+)-lepadin D and the formal total synthesis of (−)-lepadins A and C.
publishDate 2017
dc.date.none.fl_str_mv 2017
dc.type.none.fl_str_mv info:eu-repo/semantics/doctoralThesis
info:eu-repo/semantics/publishedVersion
format doctoralThesis
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/118698
http://hdl.handle.net/10803/457969
url https://hdl.handle.net/2445/118698
http://hdl.handle.net/10803/457969
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv (c) Pinto,, 2017
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Pinto,, 2017
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Universitat de Barcelona
publisher.none.fl_str_mv Universitat de Barcelona
dc.source.none.fl_str_mv Tesis Doctorals - Departament - 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 15,300719

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