Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolide

Attempts to synthesize the natural product macrolide polyketide (–)-callyspongiolide have drawn great interest</p><p>because of its potent cytotoxic activity. Its total synthesis has proven to be difficult, however, due to its</p><p>challenging structure. The influence of the...

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Autores: Urbina, Andrea, Calbó Zabala, Arnau, Llor Brunés, Núria, Bosch Mestres, Jordi, Amat Tusón, Mercedes
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2025
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/227643
Acceso en línea:https://hdl.handle.net/2445/227643
Access Level:acceso abierto
Palabra clave:Metàtesi (Química)
Compostos bioactius
Síntesi orgànica
Alcaloides
Metathesis (Chemistry)
Bioactive compounds
Organic synthesis
Alkaloids
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spelling Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolideUrbina, AndreaCalbó Zabala, ArnauLlor Brunés, NúriaBosch Mestres, JordiAmat Tusón, MercedesMetàtesi (Química)Compostos bioactiusSíntesi orgànicaAlcaloidesMetathesis (Chemistry)Bioactive compoundsOrganic synthesisAlkaloidsAttempts to synthesize the natural product macrolide polyketide (–)-callyspongiolide have drawn great interest</p><p>because of its potent cytotoxic activity. Its total synthesis has proven to be difficult, however, due to its</p><p>challenging structure. The influence of the configuration of a homoallylic stereocenter on the closure of a 14-</p><p>membered macrocyclic carbonate by ring-closing metathesis (RCM) from two epimeric dienes is described. The</p><p>results offer some insights into the structural features which contribute to hampering the closure of the</p><p>macrocyclic core of the macrolide polyketide. A formal synthesis of the marine macrolide (–)-callyspongiolide is</p><p>also reported using a RCM approach (C10-C11 bond formed) from analogous dienes bearing an α,β-unsaturated</p><p>ester instead of a carbonateMichigan Publishing2026202620252026info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion11 p.application/pdfhttps://hdl.handle.net/2445/227643Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésReproducció del document publicat a: https://doi.org/10.24820/ark.5550190.p012.470Arkivoc, 2025https://doi.org/10.24820/ark.5550190.p012.470cc-by-nc (c) ARKAT-USA, 2025http://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/openAccessoai:recercat.cat:2445/2276432026-05-29T05:05:01Z
dc.title.none.fl_str_mv Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolide
title Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolide
spellingShingle Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolide
Urbina, Andrea
Metàtesi (Química)
Compostos bioactius
Síntesi orgànica
Alcaloides
Metathesis (Chemistry)
Bioactive compounds
Organic synthesis
Alkaloids
title_short Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolide
title_full Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolide
title_fullStr Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolide
title_full_unstemmed Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolide
title_sort Ring-closing metathesis studies in the context of the formal synthesis of themarine macrolide (–)-callyspongiolide
dc.creator.none.fl_str_mv Urbina, Andrea
Calbó Zabala, Arnau
Llor Brunés, Núria
Bosch Mestres, Jordi
Amat Tusón, Mercedes
author Urbina, Andrea
author_facet Urbina, Andrea
Calbó Zabala, Arnau
Llor Brunés, Núria
Bosch Mestres, Jordi
Amat Tusón, Mercedes
author_role author
author2 Calbó Zabala, Arnau
Llor Brunés, Núria
Bosch Mestres, Jordi
Amat Tusón, Mercedes
author2_role author
author
author
author
dc.subject.none.fl_str_mv Metàtesi (Química)
Compostos bioactius
Síntesi orgànica
Alcaloides
Metathesis (Chemistry)
Bioactive compounds
Organic synthesis
Alkaloids
topic Metàtesi (Química)
Compostos bioactius
Síntesi orgànica
Alcaloides
Metathesis (Chemistry)
Bioactive compounds
Organic synthesis
Alkaloids
description Attempts to synthesize the natural product macrolide polyketide (–)-callyspongiolide have drawn great interest</p><p>because of its potent cytotoxic activity. Its total synthesis has proven to be difficult, however, due to its</p><p>challenging structure. The influence of the configuration of a homoallylic stereocenter on the closure of a 14-</p><p>membered macrocyclic carbonate by ring-closing metathesis (RCM) from two epimeric dienes is described. The</p><p>results offer some insights into the structural features which contribute to hampering the closure of the</p><p>macrocyclic core of the macrolide polyketide. A formal synthesis of the marine macrolide (–)-callyspongiolide is</p><p>also reported using a RCM approach (C10-C11 bond formed) from analogous dienes bearing an α,β-unsaturated</p><p>ester instead of a carbonate
publishDate 2025
dc.date.none.fl_str_mv 2025
2026
2026
2026
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/2445/227643
url https://hdl.handle.net/2445/227643
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/10.24820/ark.5550190.p012.470
Arkivoc, 2025
https://doi.org/10.24820/ark.5550190.p012.470
dc.rights.none.fl_str_mv cc-by-nc (c) ARKAT-USA, 2025
http://creativecommons.org/licenses/by-nc/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by-nc (c) ARKAT-USA, 2025
http://creativecommons.org/licenses/by-nc/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 11 p.
application/pdf
dc.publisher.none.fl_str_mv Michigan Publishing
publisher.none.fl_str_mv Michigan Publishing
dc.source.none.fl_str_mv Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,812429

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