Hypervalent iodine-mediated oxygenative phenol dearomatization reactions |
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Authors: | Laurent Pouysé gu,Tony Garnier,Jaime Charris,Sté phane Quideau |
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Affiliation: | a Université de Bordeaux, Institut des Sciences Moléculaires (CNRS-UMR 5255) and Institut Européen de Chimie et Biologie, 2 rue Robert Escarpit, 33607 Pessac Cedex, France b Universidad de Los Andes, Laboratorio de Productos Naturales, Facultad de Farmacia y Bioanálisis, 5101 Mérida, Venezuela c Universidad Central de Venezuela, Laboratorio de Síntesis Orgánica, 1041-A Caracas, Venezuela |
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Abstract: | Both λ3- and λ5-iodanes have proven to be useful reagents in the oxygenative dearomatization of phenols, and exploitations of their chemistry in the conception of both substrate- and reagent-controlled asymmetric variants of such a transformation of great value for natural product synthesis have shown evident signs of success. Moreover, the use of stabilized IBX (i.e., SIBX) in our methodology for O-demethylation of 2-methoxyphenols, which relies on the same key oxygenating dearomatization event, is reported here to be much more efficacious than that of IBX itself in the chemoselective one-step conversion of homovanillyl alcohol into hydroxytyrosol, and bergenin into norbergenin. |
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Keywords: | Hypervalent iodine SIBX Phenol dearomatization Demethylation Cyclohexadienones Quinone monoketal Quinol Asymmetric synthesis |
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