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Issue 18, 2013
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Chemoenzymatic synthesis of monocyclic arene oxides and arene hydrates from substituted benzene substrates

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Abstract

Enantiopure cis-dihydrodiol bacterial metabolites of substituted benzene substrates were used as precursors, in a chemoenzymatic synthesis of the corresponding benzene oxides and of a substituted oxepine, via dihydrobenzene oxide intermediates. A rapid total racemization of the substituted benzene 2,3-oxides was found to have occurred, via their oxepine valence tautomers, in accord with predictions and theoretical calculations. Reduction of a substituted arene oxide to yield a racemic arene hydrate was observed. Arene hydrates have also been synthesised, in enantiopure form, from the corresponding dihydroarene oxide or trans-bromoacetate precursors. Biotransformation of one arene hydrate enantiomer resulted in a toluene-dioxygenase catalysed cis-dihydroxylation to yield a benzene cis-triol metabolite.

Graphical abstract: Chemoenzymatic synthesis of monocyclic arene oxides and arene hydrates from substituted benzene substrates

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Publication details

The article was received on 25 Jan 2013, accepted on 13 Mar 2013 and first published on 26 Mar 2013


Article type: Paper
DOI: 10.1039/C3OB40166A
Org. Biomol. Chem., 2013,11, 3020-3029

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    Chemoenzymatic synthesis of monocyclic arene oxides and arene hydrates from substituted benzene substrates

    D. R. Boyd, N. D. Sharma, V. Ljubez, P. K. M. McGeehin, P. J. Stevenson, M. Blain and C. C. R. Allen, Org. Biomol. Chem., 2013, 11, 3020
    DOI: 10.1039/C3OB40166A

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