The diaryl ether possessing a chlorine atom has been synthesized as a model study on a synthesis of vancomycin class glycopeptide antibiotics. Thallium (III) oxidation of the bisphenol derivative followed by selective reduction provided the corresponding cyclic product in moderate overall yield. Con
Synthesis of the bis-diaryl ether fragment of vancomycin via enzymatic oxidative phenolic coupling
β Scribed by Ivica Malnar; Charles J Sih
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 176 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The bis-diaryl ether cross-linked amino acid fragment, which constitutes the upper part of a vancomycin aglycone framework, was synthesized for the first time using an enzymatic oxidative phenolic coupling methodology. This was achieved via two peroxidase-catalyzed reactions of three amino acid derivatives, 2, 3a, and 4. Other C-O and C-C hetero and homo coupling products were also obtained.
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