Four-Step Synthesis of (−)-4-epi-Presilphiperfolan-8α-ol by Intramolecular Iron Hydride Atom Transfer-Mediated Ketone-Alkene Coupling and Studies to Access trans-Hydrindanols with a Botryane Scaffold
dc.contributor.author | Saladrigas, Mar | |
dc.contributor.author | Gómez Bengoa, Enrique | |
dc.contributor.author | Bonjoch, Josep | |
dc.contributor.author | Bradshaw, Ben | |
dc.date.accessioned | 2023-03-28T14:47:39Z | |
dc.date.available | 2023-03-28T14:47:39Z | |
dc.date.issued | 2023-03 | |
dc.identifier.citation | Chemistry - A European Journal 29(15) : (2023) // Article ID e202203286 | es_ES |
dc.identifier.issn | 1521-3765 | |
dc.identifier.uri | http://hdl.handle.net/10810/60527 | |
dc.description.abstract | From an (R)-(+)-pulegone-derived building block that incorporates the stereo-defined tertiary carbon bearing a methyl group, as found in the targeted sesquiterpenoid, a four-step synthesis of (−)-4-epi-presilphiperfolan-8-α-ol was achieved. The key processes involved are a ring-closing metathesis leading to a bridged alkene-tethered ketone and its subsequent FeIII-mediated metal-hydride atom transfer (MHAT) transannular cyclization. This synthetic method, implying an irreversible addition of a carbon-centered radical upon a ketone by means of a hydrogen atom transfer upon the alkoxy radical intermediate, was also applied in the synthesis of trans-fused hydrindanols structurally related to botrydial compounds. | es_ES |
dc.description.sponsorship | Financial support for this research was provided by the Grants PID2019-104188GB-I00 and PID2019-110008GB-I00 funded by MCIN/AEI/10.13039/501100011033. We also thank SGIker (UPV/EHU) for providing human and computational resources. B.B. acknowledges the Serra Hunter program (Generalitat de Catalunya). | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | Wiley | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/PID2019-104188GB-I00 | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/PID2019-110008GB-I00 | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by/3.0/es/ | * |
dc.subject | c-c coupling | es_ES |
dc.subject | natural products | es_ES |
dc.subject | radical reactions | es_ES |
dc.subject | strained molecules | es_ES |
dc.subject | triquinanes | es_ES |
dc.title | Four-Step Synthesis of (−)-4-epi-Presilphiperfolan-8α-ol by Intramolecular Iron Hydride Atom Transfer-Mediated Ketone-Alkene Coupling and Studies to Access trans-Hydrindanols with a Botryane Scaffold | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | © 2022 The Authors. Chemistry - A European Journal 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 cited. | es_ES |
dc.rights.holder | Atribución 3.0 España | * |
dc.relation.publisherversion | https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202203286 | es_ES |
dc.identifier.doi | 10.1002/chem.202203286 | |
dc.departamentoes | Química orgánica I | es_ES |
dc.departamentoeu | Kimika organikoa I | es_ES |
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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 cited.