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
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
