Transformation of protoberberines into benzo[C]phenanthridines a novel and efficient synthesis of antitumor benzo[C]phenanthridine alkaloids, fagaronine and nitidine

✍ Scribed by Miyoji Hanaoka; Hiroshi Yamagishi; Mari Marutani; Chisato Mukai

• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 259 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81554-9

✦ Synopsis

Antileukemic benzotclphenanthridine alkaloids, fagaronine (l(Y) and nitidine (1~) were synthesized from the corresponding protoberberines through C6-N bond fission and subsequent cyclization between C6 and Cl3 position of the protoberberines. Fully aromatized 2,3,8,9_tetraoxygenated benzo[clphenanthridine alkaloids, fagaronine (la) and nitidine (1~1, isolated from ZanthoxyZum and Fagara species (Rutaceae), 1,2) were found to exhibit considerably strong antileukemic activities1'3) in L-1210 and P-388 systems in mice. Because of these potential pharmacological activities, much attention have so far been paid on the synthesis of fagaronine (la)4) and nitidine (l~).~' Recently we have achieved 6) the first biomimetic transformation of protoberberine alkaloid, berberine into benzo[clphenanthridine alkaloid, chelerythrine. Our endeavor is now focused on the development of the general Me c : f?tR%CH, 2 AMe Me berberine chelerythrine