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| - Regiocontrolled Synthesis of the Antitumor Antibiotic AT2433-A1
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| - The indolo[2,3-a]carbazole glycosides are potent antitumor antibiotics currently undergoing clinicaltrials for the treatment of numerous types of cancer. AT2433-A1 is the most complex member ofthis family of compounds possessing a unique disaccharide with a sensitive aminodeoxysugar andan unsymmetric aglycon. The synthesis of this natural product requires a method for glycosylationthat sets the stereochemistry of the anomeric center and the regiochemistry of the aglycon. Thesegoals were accomplished by carrying out the Mannich cyclization of a bis-3,4-(3-indolyl)succinimideto give a key class of indoline intermediates that could be glycosylated stereoselectively with complexcarbohydrates without hydroxyl protection or activation. The regiochemistry of the Mannichcyclization was precisely controlled by choosing between kinetic or thermodynamic conditions. Thisstrategy culminated in the first synthesis of the antitumor antibiotic AT2433-A1.
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