Synthetic Approaches to Indolo[2,3-a]carbazole alkaloids. Syntheses of arcyriaflavin A and AT2433-B aglycone

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Abstract

Ozonolysis of tetrahydrophthalimides 17 and 18 or cyclohexene diester 25 and treatment of the intermediate dialdehydes (19,20,26) with an arylhydrazine affords the corresponding bis-arylhydrazones (21-24,27,28). Exposure of 21 and 23 to PSSE in CH3NO2 gives the indolo[2,3-a]carbazole alkaloids arcyriaflavin A (8) and AT2433-B aglycone (29) in low yield. bis-Phenylhydrazones (osazones) (33,34,42,44) of cyclohexandiones were synthesized by m-CPBA oxidation of 4,5-bis(trimethylsilyloxy)tetrahydrophthalimides followed by treatment of the presumed intermediate 1,2-cyclohexanediones with an arylhydrazine. These osazones were cyclized to the corresponding indolo[2,3-a]carbazoles with PPSE. © 1992.

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Gribble, G. W., & Berthel, S. J. (1992). Synthetic Approaches to Indolo[2,3-a]carbazole alkaloids. Syntheses of arcyriaflavin A and AT2433-B aglycone. Tetrahedron, 48(41), 8869–8880. https://doi.org/10.1016/S0040-4020(01)81986-4

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