Publication
From Pyridine to (-)-Agelastatin A
| dc.contributor.author | Vale, João R. | |
| dc.contributor.author | Fortunato, Milene A. G. | |
| dc.contributor.author | Andrade, Késsia H. S. | |
| dc.contributor.author | Rocha, Ângelo M. R. | |
| dc.contributor.author | Afonso, Carlos | |
| dc.contributor.author | Siopa, Filipa | |
| dc.date.accessioned | 2024-01-19T17:27:12Z | |
| dc.date.available | 2024-01-19T17:27:12Z | |
| dc.date.issued | 2023-06 | |
| dc.date.updated | 2023-10-25T17:18:01Z | |
| dc.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. | pt_PT |
| dc.description.abstract | (−)-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. | pt_PT |
| dc.description.sponsorship | 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). | pt_PT |
| dc.description.version | info:eu-repo/semantics/publishedVersion | pt_PT |
| dc.identifier.citation | 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 | pt_PT |
| dc.identifier.doi | 10.1002/adsc.202300560 | pt_PT |
| dc.identifier.issn | 1615-4150 | |
| dc.identifier.issn | 1615-4169 | |
| dc.identifier.slug | cv-prod-3290188 | |
| dc.identifier.uri | http://hdl.handle.net/10451/61993 | |
| dc.language.iso | eng | pt_PT |
| dc.peerreviewed | yes | pt_PT |
| dc.publisher | Wiley | pt_PT |
| dc.relation | Research Institute for Medicines | |
| dc.relation | Research Institute for Medicines | |
| dc.relation | Diazo-free C-H insertion of acylsilanes towards new cyclic silanes. | |
| dc.relation | Synthetic valorization of bio-renewable resources to bioactive highly functionalized molecules | |
| dc.relation | Chemical engineered extracts of Portuguese biorenewable resources to the synthesis of diverse natural products hybrids towards new bioactive entities | |
| dc.relation.publisherversion | https://onlinelibrary.wiley.com/doi/10.1002/adsc.202300560 | pt_PT |
| dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | pt_PT |
| dc.title | From Pyridine to (-)-Agelastatin A | pt_PT |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.awardTitle | Research Institute for Medicines | |
| oaire.awardTitle | Research Institute for Medicines | |
| oaire.awardTitle | Diazo-free C-H insertion of acylsilanes towards new cyclic silanes. | |
| oaire.awardTitle | Synthetic valorization of bio-renewable resources to bioactive highly functionalized molecules | |
| oaire.awardTitle | Chemical engineered extracts of Portuguese biorenewable resources to the synthesis of diverse natural products hybrids towards new bioactive entities | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT/3599-PPCDT/2022.08559.PTDC/PT | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04138%2F2020/PT | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04138%2F2020/PT | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT//SFRH%2FBD%2F120119%2F2016/PT | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT/OE/SFRH%2FBD%2F148211%2F2019/PT | |
| oaire.awardURI | info:eu-repo/grantAgreement/FCT//2021.06598.BD/PT | |
| oaire.citation.endPage | 2247 | pt_PT |
| oaire.citation.issue | 13 | pt_PT |
| oaire.citation.startPage | 2240 | pt_PT |
| oaire.citation.title | Advanced Synthesis & Catalysis | pt_PT |
| oaire.citation.volume | 365 | pt_PT |
| oaire.fundingStream | 3599-PPCDT | |
| oaire.fundingStream | 6817 - DCRRNI ID | |
| oaire.fundingStream | 6817 - DCRRNI ID | |
| oaire.fundingStream | OE | |
| person.familyName | Vale | |
| person.familyName | Gamito Fortunato | |
| person.familyName | Mateus Afonso | |
| person.familyName | Deslgado Siopa | |
| person.givenName | João | |
| person.givenName | Milene Andreia | |
| person.givenName | Carlos Alberto | |
| person.givenName | Filipa Alexandra | |
| person.identifier.ciencia-id | DF1D-6E5E-9EE7 | |
| person.identifier.ciencia-id | AA16-A885-3ABD | |
| person.identifier.ciencia-id | 6319-2E4C-5BE1 | |
| person.identifier.ciencia-id | 6A16-150F-A9F9 | |
| person.identifier.orcid | 0000-0003-0411-9618 | |
| person.identifier.orcid | 0000-0003-1072-0709 | |
| person.identifier.orcid | 0000-0002-7284-5948 | |
| person.identifier.orcid | 0000-0002-4514-9154 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.identifier | http://doi.org/10.13039/501100001871 | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| project.funder.name | Fundação para a Ciência e a Tecnologia | |
| rcaap.cv.cienciaid | 6A16-150F-A9F9 | Filipa Alexandra Delgado Siopa | |
| rcaap.rights | openAccess | pt_PT |
| rcaap.type | article | pt_PT |
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