Intermolecular benzyne cycloaddition (IBC), a versatile approach to benzophenanthridine antitumor alkaloids. Formal synthesis of nitidine and chelerythrine

G Martin, E Guitian, L Castedo…

Index: Martin, Gloria; Guitian, Enrique; Castedo, Luis; Saa, Jose M. Journal of Organic Chemistry, 1992 , vol. 57, # 22 p. 5907 - 5911

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Citation Number: 32

Abstract

A new approach to the synthesis of benzophenanthridine alkaloids is described which is based on cycloaddition of arynes to pyrrolinediones, the pyrrolinediones behaving as aza diene equivalents. The synthesis of 2, 3, 8, 9-substituted benzophenanthridines and the regioselective synthesis of a 2, 3, 7, &substituted benzophenanthridine were performed. The formal synthesis of chelerythrine and the antitumor alkaloid nitidine is described.