Utilization of a Tandem Michael-Dieckmann Reaction to Synthesize Orixalone A

Author(s): Sungwoon Choi , Gregory D. Cuny , Kyungae Lee .

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 1 , 2006

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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

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Article Details

VOLUME: 3
ISSUE: 1
Year: 2006
Page: [68 - 72]
Pages: 5
DOI: 10.2174/157017806774964378

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