Total synthesis of oxyfagaronine, phenolic benzo[c]phenanthridine and general synthetic way of 2,3,7,8- and 2,3,8,9-tetrasubstituted benzo[c]phenanthridine alkaloids.
Benzo[c]phenanthridine alkaloids such as oxynitidine, oxysanguinarine, oxyavicine and phenolic oxyfagaronine were synthesized from easily available starting benzonitriles 5 and toluamides 6 using a lithiated toluamide-benzonitrile cycloaddition reaction. The coupling reaction provided 3-arylisoquinolinones that were transformed to the benzo[c]phenanthridones. This method is highly efficient and could be useful for preparing diverse substituted aromatic benzo[c]phenanthridine compounds on a multi gram scale.
Le
Thanh Nguyen
TN
College of Pharmacy and Research Institute of Drug Development, Chonnam National University, Kwangju, South Korea.
Cho
Won-Jea
WJ
D000470:Alkaloids / Q000138:chemical synthesis / Q000494:pharmacology; D000577:Amides / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D008956:Models, Chemical; D009570:Nitriles / Q000737:chemistry; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000494:pharmacology
D000470:Alkaloids; D000577:Amides; D000970:Antineoplastic Agents; D009570:Nitriles; D010617:Phenanthridines; C511013:oxyavicine; C511014:oxysanguinarine; C511015:oxynitidine; C014356:benzonitrile