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Open AccessFeature PaperCommunication
Molecules 2018, 23(10), 2619; https://doi.org/10.3390/molecules23102619

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

1
Institut de Chimie de Nice, Université Cote d’Azur, CNRS, Parc Valrose, 06108 Nice CEDEX 2, France
2
Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway, University Road, H91 TK33 Galway, Ireland
*
Author to whom correspondence should be addressed.
Received: 21 September 2018 / Revised: 6 October 2018 / Accepted: 10 October 2018 / Published: 12 October 2018
(This article belongs to the Special Issue Biocatalysis in Organic Synthesis)
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Abstract

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 [6.3.1.01,6.04,12] 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. View Full-Text
Keywords: cage structure; biocatalysis; phenolics; molecular complexity; sustainable chemistry cage structure; biocatalysis; phenolics; molecular complexity; sustainable chemistry
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Bouges, H.; Calabro, K.; Thomas, O.P.; Antoniotti, S. Unusual Polycyclic Fused Product by Oxidative Enzymatic Dimerisation of 5-methylpyrogallol Catalysed by Horseradish Peroxidase/H2O2. Molecules 2018, 23, 2619.

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