Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium

We have investigated the oxidative behaviour of natural compounds such as methyl abietate (1), farnesyl acetate (2), α-ionone (3), β-ionone (4), methyl linolelaidate (5), methyl linolenate (6) and bergamottin (7) with the oxidant system methyltrioxo-rhenium/H(2)O(2)/pyridine. The reactions, performe...

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Autores principales: Amato, Maria E., Ballistreri, Francesco P., Pappalardo, Andrea, Tomaselli, Gaetano A., Toscano, Rosa M., Sfrazzetto, Giuseppe Trusso
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270049/
https://www.ncbi.nlm.nih.gov/pubmed/24213654
http://dx.doi.org/10.3390/molecules181113754
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author Amato, Maria E.
Ballistreri, Francesco P.
Pappalardo, Andrea
Tomaselli, Gaetano A.
Toscano, Rosa M.
Sfrazzetto, Giuseppe Trusso
author_facet Amato, Maria E.
Ballistreri, Francesco P.
Pappalardo, Andrea
Tomaselli, Gaetano A.
Toscano, Rosa M.
Sfrazzetto, Giuseppe Trusso
author_sort Amato, Maria E.
collection PubMed
description We have investigated the oxidative behaviour of natural compounds such as methyl abietate (1), farnesyl acetate (2), α-ionone (3), β-ionone (4), methyl linolelaidate (5), methyl linolenate (6) and bergamottin (7) with the oxidant system methyltrioxo-rhenium/H(2)O(2)/pyridine. The reactions, performed in CH(2)Cl(2)/H(2)O at 25 °C, have shown good regio- and stereoselectivity. The oxidation products were isolated by HPLC or silica gel chromatography and characterized by MS(EI), (1)H-, (13)C-NMR, APT, gCOSY, HSQC, TOCSY and NOESY measurements. The selectivity seems to be controlled by the nucleophilicity of double bonds and by stereoelectronic and steric effects.
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spelling pubmed-62700492018-12-20 Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium Amato, Maria E. Ballistreri, Francesco P. Pappalardo, Andrea Tomaselli, Gaetano A. Toscano, Rosa M. Sfrazzetto, Giuseppe Trusso Molecules Article We have investigated the oxidative behaviour of natural compounds such as methyl abietate (1), farnesyl acetate (2), α-ionone (3), β-ionone (4), methyl linolelaidate (5), methyl linolenate (6) and bergamottin (7) with the oxidant system methyltrioxo-rhenium/H(2)O(2)/pyridine. The reactions, performed in CH(2)Cl(2)/H(2)O at 25 °C, have shown good regio- and stereoselectivity. The oxidation products were isolated by HPLC or silica gel chromatography and characterized by MS(EI), (1)H-, (13)C-NMR, APT, gCOSY, HSQC, TOCSY and NOESY measurements. The selectivity seems to be controlled by the nucleophilicity of double bonds and by stereoelectronic and steric effects. MDPI 2013-11-07 /pmc/articles/PMC6270049/ /pubmed/24213654 http://dx.doi.org/10.3390/molecules181113754 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Amato, Maria E.
Ballistreri, Francesco P.
Pappalardo, Andrea
Tomaselli, Gaetano A.
Toscano, Rosa M.
Sfrazzetto, Giuseppe Trusso
Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium
title Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium
title_full Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium
title_fullStr Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium
title_full_unstemmed Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium
title_short Selective Oxidation Reactions of Natural Compounds with Hydrogen Peroxide Mediated by Methyltrioxorhenium
title_sort selective oxidation reactions of natural compounds with hydrogen peroxide mediated by methyltrioxorhenium
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270049/
https://www.ncbi.nlm.nih.gov/pubmed/24213654
http://dx.doi.org/10.3390/molecules181113754
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