Total synthesis of lodopyridone |
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Authors: | Tobias Burckhardt Klaus Harms Ulrich Koert |
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Affiliation: | Fachbereich Chemie, Philipps-University Marburg , Hans-Meerwein-Strasse, D-35032 Marburg, Germany. |
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Abstract: | A convergent total synthesis of the structurally unprecedented alkaloid lodopyridone was achieved using a cross-coupling of an iodopyridone fragment with a quinolinethiazolylstannane. Key features of the syntheses of the pentasubstituted 4-pyridone were a 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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