Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 8581-8587 |
| Number of pages | 6 |
| Journal | Tetrahedron |
| Volume | 57 |
| Issue number | 40 |
| DOIs | |
| Publication status | Published - Oct 2001 |
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Keywords
- biotransformations
- chloroperoxidases
- benzofurans
- dihydroxylation
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A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase. / Alvarez, Ricardo G.; Hunter, Iain S.; Suckling, Colin J.; Thomas, Michael; Vitinius, Ute.
In: Tetrahedron, Vol. 57, No. 40, 10.2001, p. 8581-8587.Research output: Contribution to journal › Article
TY - JOUR
T1 - A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase
AU - Alvarez, Ricardo G.
AU - Hunter, Iain S.
AU - Suckling, Colin J.
AU - Thomas, Michael
AU - Vitinius, Ute
PY - 2001/10
Y1 - 2001/10
N2 - 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.
AB - 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.
KW - biotransformations
KW - chloroperoxidases
KW - benzofurans
KW - dihydroxylation
UR - http://dx.doi.org/10.1016/S0040-4020(01)00837-7
U2 - 10.1016/S0040-4020(01)00837-7
DO - 10.1016/S0040-4020(01)00837-7
M3 - Article
VL - 57
SP - 8581
EP - 8587
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 40
ER -