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
Full text not available in this repository. (Request a copy from the Strathclyde author)Abstract
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 |
| Subjects: | Science > Chemistry |
| Department: | Faculty of Science > Pure and Applied Chemistry Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences Unknown Department |
| Related URLs: | |
| Depositing user: | Allison Crawford |
| Date Deposited: | 05 Apr 2006 |
| Last modified: | 12 Mar 2012 10:35 |
| URI: | http://strathprints.strath.ac.uk/id/eprint/720 |
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