Beilstein J. Org. Chem.2013,9, 2042–2047, doi:10.3762/bjoc.9.242
alkaloid; total synthesis; Findings
(−)-Epimyrtine, isolated from Vaccinium myrtillus (Ericaceae) [1][2], is a quinolizidinealkaloid. This alkaloid family exhibits potential pharmacological properties such as anticancer, antibacterial, antiviral and anti-inflammation activities [3][4][5]. This alkaloid
-alanine. The key step to access the enantiopure pyridone intermediate was achieved by a gold-mediated cyclization. Finally, various transformations afforded the natural product in a few steps and good overall yield.
Keywords: epimyrtine; gold; gold catalysis; heterocycles; hydroamination; quinolizidine
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Graphical Abstract
Scheme 1:
Previously reported approach from β-aminoynones for the synthesis of pyridones.