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A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase

Alvarez, Ricardo G. and Hunter, Iain S. and Suckling, Colin J. and Thomas, Michael and Vitinius, Ute (2001) A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase. Tetrahedron, 57 (40). pp. 8581-8587. ISSN 0040-4020

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Abstract The oxidation of 3-alkyl benzofurans, indoles, and a benzothiophene by the chloroperoxidase from Caldariomyces fumago has been investigated. Under conditions in which the catalase activity of chloroperoxidase was minimised in the presence of chloride and hydrogen peroxide, 3-methylbenzothiophene was oxidised at sulfur but the indoles (5-9) and benzofurans (1-4) gave 2,3-diols as initial products. In the case of N-unsubstituted indoles, these tautomerised to give the corresponding lactam. In contrast, the diols (predominantly trans) formed from the benzofurans were sufficiently stable for isolation and full characterisation. This novel reaction has the potential to be developed into a useful synthetic biotransformation.

Item type: Article
ID code: 720
Keywords: biotransformations, chloroperoxidases, benzofurans, dihydroxylation, Chemistry, Biochemistry, Organic Chemistry, Drug Discovery
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences
Unknown Department
Depositing user: Allison Crawford
Date Deposited: 05 Apr 2006
Last modified: 21 May 2015 08:18

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