Total synthesis of lodopyridone.
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.
Fachbereich Chemie, Philipps-University Marburg, Hans-Meerwein-Strasse, D-35032 Marburg, Germany.
Tobias
T
Burckhardt
Klaus
K
Harms
Ulrich
U
Koert
D039903:Actinobacteria / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D011728:Pyridones; C546479:lodopyridone; C534143:4-pyridone