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

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

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allyl Compounds / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Pyridines / chemical synthesis*
  • Spectrometry, Mass, Electrospray Ionization
  • Stereoisomerism
  • Triazines / chemistry*

Substances

  • Allyl Compounds
  • Pyridines
  • Triazines
  • 1,2,4-triazine