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

Sungwoon      Choi; Gregory   D.   Cuny; Kyungae      Lee

doi:10.2174/157017806774964378

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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Letters in Organic Chemistry

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

Volume: 3 Issue: 1

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

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Keywords: 4-hydroxy-2-quinolinones, tandem Michael-Dieckmann reaction, orixalone A

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.

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Choi Sungwoon, Cuny D. Gregory and Lee Kyungae, Utilization of a Tandem Michael-Dieckmann Reaction to Synthesize Orixalone A, Letters in Organic Chemistry 2006; 3 (1) . https://dx.doi.org/10.2174/157017806774964378