Unusual Polycyclic Fused Product by Oxidative Enzymatic Dimerisation of 5-methylpyrogallol Catalysed by Horseradish Peroxidase/H2O2 - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue Molecules Année : 2018

Unusual Polycyclic Fused Product by Oxidative Enzymatic Dimerisation of 5-methylpyrogallol Catalysed by Horseradish Peroxidase/H2O2

Résumé

During investigations on the peroxidase-catalysed oxidation of polyhydroxylated monoaromatic substrates such as 5-methylpyrogallol, we observed a spectacular dimerisation proceeding by dearomatisation in contrast with most common reaction patterns involving phenolics oxidation and dimerization. A tetracyclic fused product featuring an unusual 2-oxatetracyclo [6.3.1.0 1,6 .0 4,12 ] dodecan-3-one core was obtained and characterized by combined NMR techniques and high resolution mass spectroscopy (HRMS). This is an example of a spontaneous cascade triggered by a simple enzymatic reaction that could provide new options for biosynthetic hypothesis and a synthetic method to access this complex core in one operation.
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hal-02357719 , version 1 (10-11-2019)

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Hélène Bouges, Kevin Calabro, Olivier Thomas, Sylvain Antoniotti. Unusual Polycyclic Fused Product by Oxidative Enzymatic Dimerisation of 5-methylpyrogallol Catalysed by Horseradish Peroxidase/H2O2. Molecules, 2018, 23 (10), pp.2619. ⟨10.3390/molecules23102619⟩. ⟨hal-02357719⟩
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