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Issue 36, 2012
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Toluene dioxygenase-catalyzed cis-dihydroxylation of benzo[b]thiophenes and benzo[b]furans: synthesis of benzo[b]thiophene 2,3-oxide

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Abstract

Enzymatic cis-dihydroxylation of benzo[b]thiophene, benzo[b]furan and several methyl substituted derivatives was found to occur in both the carbocyclic and heterocyclic rings. Relative and absolute configurations and enantiopurities of the resulting dihydrodiols were determined. Hydrogenation of the alkene bond in carbocyclic cis-dihydrodiols and ring-opening epimerization/reduction reactions of heterocyclic cis/trans-dihydrodiols were also studied. The relatively stable heterocyclic dihydrodiols of benzo[b]thiophene and benzo[b]furan showed a strong preference for the trans configuration in aqueous solutions. The 2,3-dihydrodiol metabolite of benzo[b]thiophene was utilized as a precursor in the chemoenzymatic synthesis of the unstable arene oxide, benzo[b]thiophene 2,3-oxide.

Graphical abstract: Toluene dioxygenase-catalyzed cis-dihydroxylation of benzo[b]thiophenes and benzo[b]furans: synthesis of benzo[b]thiophene 2,3-oxide

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Supplementary files

Article information


Submitted
11 Jun 2012
Accepted
23 Jul 2012
First published
09 Aug 2012

Org. Biomol. Chem., 2012,10, 7292-7304
Article type
Paper

Toluene dioxygenase-catalyzed cis-dihydroxylation of benzo[b]thiophenes and benzo[b]furans: synthesis of benzo[b]thiophene 2,3-oxide

D. R. Boyd, N. D. Sharma, I. N. Brannigan, T. A. Evans, S. A. Haughey, B. T. McMurray, J. F. Malone, P. B. A. McIntyre, P. J. Stevenson and C. C. R. Allen, Org. Biomol. Chem., 2012, 10, 7292
DOI: 10.1039/C2OB26120K

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