Chemical transformation of protoberberines. XIII. A novel and efficient synthesis of antitumor benzo [c] phenanthridine alkaloids, nitidine and fagaronine.

M HANAOKA, H YAMAGISHI, M MARUTANI…

Index: Hanaoka; Yamagishi; Marutani; Mukai Chemical and Pharmaceutical Bulletin, 1987 , vol. 35, # 6 p. 2348 - 2354

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Citation Number: 22

Abstract

An efficient synthesis of nitidine (1a). and fagaronine (1c), antitumor 2, 3, 8, 9- tetraoxygenated benzo [c] phenanthridine alkaloids, has been achieved via regioselective C 6-N bond cleavage, followed by consecutive oxy-functionalization and recyclization between the C 6 and C 13 positions of the starting protoberberines, pseudoberberine (3a) and O- benzyldehydrodiscretine (3b), respectively.