Extending Pummerer Reaction Chemistry. Application to the Oxidative Cyclization of Tryptophan Derivatives

The diastereoselective oxidative cyclization of a β-oxygenated tryptophan derivative is reported. This process, which utilizes a new variant of the Pummerer reaction, may have application in TMC-95A synthesis.

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Bibliographic Details
Published in:Organic letters 2004-08, Vol.6 (17), p.2849-2852
Main Authors: Feldman, Ken S, Karatjas, Andrew G
Format: Article
Language:English
Subjects:
Catalysis
Cyclization
Molecular Structure
Oxidation-Reduction
Peptides, Cyclic - chemical synthesis
Stereoisomerism
Tryptophan - analogs & derivatives
Tryptophan - chemistry
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Description
Summary:The diastereoselective oxidative cyclization of a β-oxygenated tryptophan derivative is reported. This process, which utilizes a new variant of the Pummerer reaction, may have application in TMC-95A synthesis.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol048974+