Diastereoselective synthesis of methanopyridoxazocinones

Siva S. Panda, Peter J. Steel

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

Two approaches to the synthesis of oxygen-bridged tetrahydropyridones have been developed. In the first approach, substituted pyrido[4,3-g][1,3]oxazocines derivatives were prepared by diastereoselective one-pot reactions of substituted 7-azacoumarins with enolizable ketones and non-bulky primary amines. In the second one, 3-amido-7-azacoumarins were reacted with enolizable ketones in the presence of a base to form diastereomerically pure pyrido[4,3-g][1,3]oxazocines.

Original languageEnglish (US)
Article numberst-2014-s0510-1
Pages (from-to)2654-2660
Number of pages7
JournalSynlett
Volume25
Issue number18
DOIs
Publication statusPublished - Oct 7 2014

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Keywords

  • azacoumarin
  • bridged heterocycles
  • chirality
  • diastereomer
  • synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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