Title of article
Utilization of a Tandem Michael-Dieckmann Reaction to Synthesize Orixalone A
Author/Authors
Cuny, Gregory D. Brigham Women’s Hospital and Harvard Medical School - Laboratory for Drug Discovery in Neurodegeneration, USA , Lee, Kyungae Harvard Medical School - Department of Microbiology and Molecular Genetics, USA , Choi, Sungwoon Brigham Women’s Hospital and Harvard Medical School - Laboratory for Drug Discovery in Neurodegeneration, USA
From page
68
To page
72
Abstract
A survey of bases for inducing a Dieckmann cyclization of 2-acylaminobenzoates to give 4-hydroxy-2-quinolinones revealed that hindered non-nucleophilic bases were optimal. However, for sterically demanding substrates sodium hydride performed better. A tandem Michael-Dieckmann reaction for the construction of 4-hydroxy-2-quinolinones is also presented. This methodology is utilized as a key step in the synthesis of the natural product orixalone A.
Keywords
4 , hydroxy , 2 , quinolinones , tandem Michael , Dieckmann reaction , orixalone A
Journal title
letters in organic chemistry
Journal title
letters in organic chemistry
Record number
2717953
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