Syntheses and Diels-Alder cycloaddition reactions of 4H-furo [3, 4-b] indoles. A regiospecific Diels-Alder synthesis of ellipticine

…, MG Saulnier, B Pelcman, TC Barden…

Index: Gribble; Keavy; Davis; Saulnier; Pelcman; Barden; Sibi; Olson; BelBruno Journal of Organic Chemistry, 1992 , vol. 57, # 22 p. 5878 - 5891

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Citation Number: 100

Abstract

Seven examples of the novel 4H-furo [3, 4-b] indole ring system (3-9)-a stable, synthetic analogue of indole-2, 3-quinodimethane-have been synthesized in 6-8 steps from simple indoles in overall yields of 21-28%. These 4H-furo [3, 4-b] indoles undergo Diels-Alder reactions with several dienophiles (dimethyl acetylenedicarboxylate, N-phenylmaleimide, benzyne), including ethyl acrylate, which reacts regiospecifically with furoindole 4 to afford ...