Journal
ORGANIC LETTERS
Volume 14, Issue 17, Pages 4674-4677Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol302121w
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- Deutsche Forschungs-gemeins-chaft
- Fonds der Chemischen Industrie
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A convergent total synthesis of the structurally unprecedented alkaloid lodopyridone was achieved using a cross-coupling of an lodopyridone fragment with a quinolinethiazolylstannane. Key features of the syntheses of the pentasubstituted 4-pyridone were e regioselective bromination of a 4-pyridone derived from kojic acid, a subsequent Cu-mediated introduction of the thioether, and a directed lithiation/iodination step. A chemoselective Negishi cross-coupling of a dibromothiazole and a quinolinylzinc reagent was used to assemble the chloroquinolinethiazol moiety.
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