Preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of 2-oxoaustroeupatol

From aerial parts of Austroeupatorium inulifolium was isolated the ent-nor-furano triol labdane austroeupatol 1. The compound 1 was treated with IBX showing an unexpected selectivity at the potentially oxidizable sites of the substrate yielding the 2-oxoaustroeupatol (2) and 2,19-dioxoaustroeupatol...

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Autores principales: Chacón-Morales, Pablo A., Amaro-Luis, Juan M., Rojas Fermín, Luis Beltrán, Jacquet, Rémi, Deffieux, Denis, Pouységu, Laurent, Quideau, Stéphane
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Nature Singapore 2022
Materias:
Short Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9156645/
https://www.ncbi.nlm.nih.gov/pubmed/35641706
http://dx.doi.org/10.1007/s13659-022-00343-2
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author Chacón-Morales, Pablo A.
Amaro-Luis, Juan M.
Rojas Fermín, Luis Beltrán
Jacquet, Rémi
Deffieux, Denis
Pouységu, Laurent
Quideau, Stéphane
author_facet Chacón-Morales, Pablo A.
Amaro-Luis, Juan M.
Rojas Fermín, Luis Beltrán
Jacquet, Rémi
Deffieux, Denis
Pouységu, Laurent
Quideau, Stéphane
author_sort Chacón-Morales, Pablo A.
collection PubMed
description From aerial parts of Austroeupatorium inulifolium was isolated the ent-nor-furano triol labdane austroeupatol 1. The compound 1 was treated with IBX showing an unexpected selectivity at the potentially oxidizable sites of the substrate yielding the 2-oxoaustroeupatol (2) and 2,19-dioxoaustroeupatol (3). The treatment of 2 with sodium periodate yields a heterocyclic derivative (ε-caprolactone derivate 4) formed by oxidative cleavage and unexpected intramolecular attack of the hydroxymethylene (C-19) oxygen to the ketonic carbon (C-2). A plausible mechanistic pathway for the obtention of compound 4 is proposed. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s13659-022-00343-2.
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spelling pubmed-91566452022-06-02 Preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of 2-oxoaustroeupatol Chacón-Morales, Pablo A. Amaro-Luis, Juan M. Rojas Fermín, Luis Beltrán Jacquet, Rémi Deffieux, Denis Pouységu, Laurent Quideau, Stéphane Nat Prod Bioprospect Short Communication From aerial parts of Austroeupatorium inulifolium was isolated the ent-nor-furano triol labdane austroeupatol 1. The compound 1 was treated with IBX showing an unexpected selectivity at the potentially oxidizable sites of the substrate yielding the 2-oxoaustroeupatol (2) and 2,19-dioxoaustroeupatol (3). The treatment of 2 with sodium periodate yields a heterocyclic derivative (ε-caprolactone derivate 4) formed by oxidative cleavage and unexpected intramolecular attack of the hydroxymethylene (C-19) oxygen to the ketonic carbon (C-2). A plausible mechanistic pathway for the obtention of compound 4 is proposed. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s13659-022-00343-2. Springer Nature Singapore 2022-06-01 /pmc/articles/PMC9156645/ /pubmed/35641706 http://dx.doi.org/10.1007/s13659-022-00343-2 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Short Communication
Chacón-Morales, Pablo A.
Amaro-Luis, Juan M.
Rojas Fermín, Luis Beltrán
Jacquet, Rémi
Deffieux, Denis
Pouységu, Laurent
Quideau, Stéphane
Preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of 2-oxoaustroeupatol
title Preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of 2-oxoaustroeupatol
title_full Preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of 2-oxoaustroeupatol
title_fullStr Preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of 2-oxoaustroeupatol
title_full_unstemmed Preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of 2-oxoaustroeupatol
title_short Preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of 2-oxoaustroeupatol
title_sort preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of 2-oxoaustroeupatol
topic Short Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9156645/
https://www.ncbi.nlm.nih.gov/pubmed/35641706
http://dx.doi.org/10.1007/s13659-022-00343-2
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