From Pyridine to (-)-Agelastatin A

Detalhes bibliográficos
Autor(a) principal: Vale, João R.
Data de Publicação: 2023
Outros Autores: Fortunato, Milene A. G., Andrade, Késsia H. S., Rocha, Ângelo M. R., Afonso, Carlos, Siopa, Filipa
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10451/61993
Resumo: © 2023 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cite.
id RCAP_c3d2a114bfe8ebe03baa76a969fea138
oai_identifier_str oai:repositorio.ul.pt:10451/61993
network_acronym_str RCAP
network_name_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository_id_str 7160
spelling From Pyridine to (-)-Agelastatin A© 2023 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cite.(−)-Agelastatin A was synthetized employing a flow photorearrangement of a pyridinium salt, constructing in one step the cyclopentene core possessing the desired functionalities and relative configurations. A flow enzymatic kinetic resolution of the resulting bicyclic vinyl aziridine delivered the enantiopure precursor to the natural product. This total synthesis required the use of a single protective group. Two novel agelastatin N3-derivatives were synthesized and their cytotoxicity evaluated against a series of cancer cell lines, which corroborated the importance of unsubstituted N3 in the biological activity of (−)-agelastatin A.The authors acknowledge Fundação para a Ciência e Tecnologia (FCT) for financial support (2022.08559.PTDC, UIDB/04138/2020, UIDP/04138/2020, SFRH/BD/120119/2016, SFRH/BD/148211/2019 and 2021.06598.BD). The project leading to this application has received funding from the European Union's Horizon 2020 research and innovation programme under grant agreement No 951996. The NMR spectrometers are part of the National NMR Network (PT NMR) are partially supported by Infrastructure Project No. 022161 (co-financed by FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC).WileyRepositório da Universidade de LisboaVale, João R.Fortunato, Milene A. G.Andrade, Késsia H. S.Rocha, Ângelo M. R.Afonso, CarlosSiopa, Filipa2024-01-19T17:27:12Z2023-062023-10-25T17:18:01Z2023-06-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10451/61993engVale JR, Fortunato MAG, Andrade KHS, Rocha ÂMR, Afonso CAM, Siopa F. From pyridine to (−)‐agelastatin a. Adv Synth Catal [Internet]. 4 de julho de 2023;365(13):2240–7. Disponível em: https://onlinelibrary.wiley.com/doi/10.1002/adsc.2023005601615-4150cv-prod-329018810.1002/adsc.202300560info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-01-22T01:20:27Zoai:repositorio.ul.pt:10451/61993Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T01:56:16.648504Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv From Pyridine to (-)-Agelastatin A
title From Pyridine to (-)-Agelastatin A
spellingShingle From Pyridine to (-)-Agelastatin A
Vale, João R.
title_short From Pyridine to (-)-Agelastatin A
title_full From Pyridine to (-)-Agelastatin A
title_fullStr From Pyridine to (-)-Agelastatin A
title_full_unstemmed From Pyridine to (-)-Agelastatin A
title_sort From Pyridine to (-)-Agelastatin A
author Vale, João R.
author_facet Vale, João R.
Fortunato, Milene A. G.
Andrade, Késsia H. S.
Rocha, Ângelo M. R.
Afonso, Carlos
Siopa, Filipa
author_role author
author2 Fortunato, Milene A. G.
Andrade, Késsia H. S.
Rocha, Ângelo M. R.
Afonso, Carlos
Siopa, Filipa
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Repositório da Universidade de Lisboa
dc.contributor.author.fl_str_mv Vale, João R.
Fortunato, Milene A. G.
Andrade, Késsia H. S.
Rocha, Ângelo M. R.
Afonso, Carlos
Siopa, Filipa
description © 2023 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cite.
publishDate 2023
dc.date.none.fl_str_mv 2023-06
2023-10-25T17:18:01Z
2023-06-01T00:00:00Z
2024-01-19T17:27:12Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10451/61993
url http://hdl.handle.net/10451/61993
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Vale JR, Fortunato MAG, Andrade KHS, Rocha ÂMR, Afonso CAM, Siopa F. From pyridine to (−)‐agelastatin a. Adv Synth Catal [Internet]. 4 de julho de 2023;365(13):2240–7. Disponível em: https://onlinelibrary.wiley.com/doi/10.1002/adsc.202300560
1615-4150
cv-prod-3290188
10.1002/adsc.202300560
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
_version_ 1799137051277262848

Registros relacionados