title: A novel approach to the pyridoacridine ring system: synthesis of the topoisomerase inhibitor 13-deazaascididemin.
abstract: A novel approach to the pyridoacridine ring system of the ascididemin-type marine alkaloids is presented. This approach allows for the introduction of the ring A of the alkaloids by using a simple aromatic aldehyde building block. The viability of this approach is demonstrated with the synthesis of AK37, a bioactive deaza analogue of the alkaloid ascididemin. Starting from 3-cyano-4-methylquinoline, a sequence of regioselective homolytic benzoylation, annulation of a bromopyridine ring, and radical cyclization leads to the pentacyclic ring system.
authors: Department of Pharmacy, Center for Drug Research, Ludwig-Maximilians University of Munich, Munich, Germany.
authors: Stephan
authors: S
authors: Raeder
authors: Franz
authors: F
authors: Bracher
mesh_terms: D000166:Acridines / Q000138:chemical synthesis* / Q000494:pharmacology; D000447:Aldehydes / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis / Q000494:pharmacology; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000494:pharmacology; D059003:Topoisomerase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: C499812:AK37 compound; D000166:Acridines; D000447:Aldehydes; D000470:Alkaloids; D010618:Phenanthrolines; D059003:Topoisomerase Inhibitors