Total Synthesis of Isoriccardin C and Isoriccardin D Based on a Hydroxyl-Directed Palladium-Catalyzed Intramolecular C–H Alkenylation

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dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánica
dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS)
dc.contributor.authorLosada Castro, Pablo
dc.contributor.authorMascareñas Cid, José Luis
dc.contributor.authorGulías Costa, Moisés
dc.date.accessioned2026-05-18T12:25:14Z
dc.date.available2026-05-18T12:25:14Z
dc.date.issued2026-04-06
dc.description.abstractA concise, nine-step total synthesis of isoriccardin C and isoriccardin D has been developed. The strategy centers on the sequential installation of the four aromatic rings of the backbone by using three key transformations: Suzuki coupling, Wittig olefination, and Ullmann coupling. The pivotal step is a palladium(II)-catalyzed, intramolecular ortho-alkenylation that forges the 18-membered macrocyclic core. This streamlined route enables the total synthesis with minimal reliance on protecting groups, and its modular nature offers a versatile platform for the construction of structural analogues.
dc.description.peerreviewedSI
dc.description.sponsorshipThis work received financial support from the Spanish Government (Grants PID2022-137318OB-I00 and PID2022-136785NB-I00 funded by MCIN/AEI/10.13039/501100011033, Grant IHRC22-00009 funded by MCIN/ISCIII and the “European Union Next Generation EU/PRTR” and ORFEO–CINQA network RED2022-134287-T) and “ERDF A way of making Europe”. The authors also thank the Xunta de Galicia (Grants ED431C 2021/25, ED431C 2025/02, and ED431G 2023/03: Centro Singular de Investigación de Galicia accreditation 2023–2027. and predoctoral fellowship to P.L.) and the European Union (European Regional Development Fund-ERDF corresponding to the multiannual financial framework 2014–2020).
dc.identifier.citationLosada, P., Mascareñas, J. L., & Gulías, M. (2026). Total Synthesis of Isoriccardin C and Isoriccardin D Based on a Hydroxyl-Directed Palladium-Catalyzed Intramolecular C-H Alkenylation. "Organic letters", 28(15), 4836-4840. https://doi.org/10.1021/ACS.ORGLETT.6C00911
dc.identifier.doi10.1021/acs.orglett.6c00911
dc.identifier.issn4836–4840
dc.identifier.urihttps://hdl.handle.net/10347/47246
dc.issue.number15
dc.journal.titleOrganic Letters
dc.language.isoeng
dc.page.final4840
dc.page.initial4836
dc.publisherAmerican Chemical Society
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-137318OB-I00/ES/APLICACIONES BIOMEDICAS DE COMPLEJOS DE METALES DE TRANSICION: HERRAMIENTAS CATALITICAS Y DESARROLLO DE NUEVAS TERAPIAS ANTICANCER
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-136785NB-I00/ES/NUEVAS ESTRATEGIAS DE SINTESIS ENANTIOSELECTIVA BASADAS EN LA ACTIVACION DE ENLACES C-H MEDIANTE CATALISIS METALICA
dc.relation.publisherversionhttps://doi.org/10.1021/acs.orglett.6c00911
dc.rightsCopyright © 2026 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0 .
dc.rightsAttribution 4.0 Internationalen
dc.rights.accessRightsopen access
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectChemical synthesis
dc.subjectHydrocarbons
dc.subjectMacrocyclization
dc.subjectOlefination
dc.subjectOrganic synthesis
dc.subject.classification2306 Química orgánica
dc.subject.classification2390 Química farmacéutica
dc.subject.classification2210 Química física
dc.subject.classification3303 ingeniería y tecnología químicas
dc.titleTotal Synthesis of Isoriccardin C and Isoriccardin D Based on a Hydroxyl-Directed Palladium-Catalyzed Intramolecular C–H Alkenylation
dc.typejournal article
dc.type.hasVersionVoR
dc.volume.number28
dspace.entity.typePublication
relation.isAuthorOfPublication5ae222c9-f626-432b-aac5-da78c06ed64f
relation.isAuthorOfPublication47a6a088-27a9-412e-8422-0de4fd8af0d4
relation.isAuthorOfPublication.latestForDiscovery5ae222c9-f626-432b-aac5-da78c06ed64f

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