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- Title
Unusual Polycyclic Fused Product by Oxidative Enzymatic Dimerisation of 5-methylpyrogallol Catalysed by Horseradish Peroxidase/H2O2.
- Authors
Bouges, Hélène; Calabro, Kevin; Thomas, Olivier P.; Antoniotti, Sylvain
- 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.
- Subjects
PEROXIDASE; OXIDATION; PHENOLS; DIMERIZATION; AROMATIZATION; NUCLEAR magnetic resonance; CHEMICAL reactions
- Publication
Molecules, 2018, Vol 23, Issue 10, p2619
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules23102619