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

Ricardo G. Alvarez, Iain S. Hunter, Colin J. Suckling, Michael Thomas, Ute Vitinius

Research output: Contribution to journalArticle

21 Citations (Scopus)

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.
LanguageEnglish
Pages8581-8587
Number of pages6
JournalTetrahedron
Volume57
Issue number40
DOIs
Publication statusPublished - Oct 2001

Fingerprint

Benzofurans
Chloride Peroxidase
Indoles
Biotransformation
Lactams
Sulfur
Catalase
Hydrogen Peroxide
Chlorides
Oxidation

Keywords

  • biotransformations
  • chloroperoxidases
  • benzofurans
  • dihydroxylation

Cite this

Alvarez, Ricardo G. ; Hunter, Iain S. ; Suckling, Colin J. ; Thomas, Michael ; Vitinius, Ute. / A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase. In: Tetrahedron. 2001 ; Vol. 57, No. 40. pp. 8581-8587.
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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 journalArticle

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

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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

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