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J Org Chem. 2009 Nov 6;74(21):8343-54. doi: 10.1021/jo901761r.

Synthesis of the louisianin alkaloid family via a 1,2,4-triazine inverse-electron-demand Diels-Alder approach.

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  • 1Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.

Abstract

Isolated in 1995, the four members of the louisianin family (A, B, C and D) are simple pyridine and 2-pyridone alkaloids that display both antibacterial and anticancer activity. Herein we describe the synthesis of all four members of the louisianin family, from a conveniently prepared 1,2,4-triazine and via a common tetrasubstituted pyridine intermediate. This study includes the synthesis of louisianin B in both racemic form and as the (-)-enantiomer.

PMID:
19780559
DOI:
10.1021/jo901761r
[PubMed - indexed for MEDLINE]
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