Synthesis of the louisianin alkaloid family via a 1,2,4-triazine inverse-electron-demand Diels-Alder approach.
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.
Catozzi
Nicola
N
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
Edwards
Michael G
MG
Raw
Steven A
SA
Wasnaire
Pierre
P
Taylor
Richard J K
RJ
D000498:Allyl Compounds / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D011725:Pyridines / Q000138:chemical synthesis*; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D014227:Triazines / Q000737:chemistry*
D000498:Allyl Compounds; D011725:Pyridines; D014227:Triazines; C093444:1,2,4-triazine