Three-component synthesis of disubstituted 2H-pyrrol-2-ones: preparation of the violacein scaffold

[Display omitted] An efficient, three-component, microwave-mediated cyclization to prepare the 3,5-disubstituted 2H-pyrrol-2-one core of the bis-indole alkaloid, violacein, is described. Preliminary results indicate an iterative, thermally driven, condensation of a γ-ketoester, ammonium acetate, and...

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Bibliographic Details
Published in:Tetrahedron letters 2014-04, Vol.55 (16), p.2609-2611
Main Authors: McLaughlin, Emily C., Norman, Matthew W., Ko Ko, Thant, Stolt, Ingrid
Format: Article
Language:English
Subjects:
Alkaloids
Ammonium acetate
Analogs
Condensing
Indole alkaloids
Microwave synthesis
Polyethylene glycol
Pyrrol-2-one
Scaffolds
Synthesis (chemistry)
Tetrahedrons
Three-component cyclization
Violacein
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Summary:[Display omitted] An efficient, three-component, microwave-mediated cyclization to prepare the 3,5-disubstituted 2H-pyrrol-2-one core of the bis-indole alkaloid, violacein, is described. Preliminary results indicate an iterative, thermally driven, condensation of a γ-ketoester, ammonium acetate, and isatin in polyethylene glycol. This methodology is an effective and environmentally benign route to prepare a series of violacein analogs in good overall yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.02.111