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The total syntheses of aspidospermidine, N -methylaspidospermidine, N -acetylaspidospermidine, and aspidospermine were achieved from a common pentacyclic indoline intermediate. The common pentacyclic indoline intermediate was synthesized on a gram scale through a Stork-enamine alkylation of 1 H -pyrrolo[2,3- d ]carbazole derivatives, which were prepared through a Brønsted acid-catalyzed tandem cyclization of tryptamine-ynamide. The scalable synthesis of 1 H -pyrrolo[2,3- d ]carbazole afforded facile access and a practical approach to the Aspidosperma indole alkaloid family.

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Total Syntheses of Aspidospermidine, <i>N</i>-Methylaspidospermidine, <i>N</i>-Acetylaspidospermidine, and Aspidospermine via a Tandem Cyclization of Tryptamine-Ynamide

Total Syntheses of Aspidospermidine, N-Methylaspidospermidine, N-Acetylaspidospermidine, and Aspidospermine via a Tandem Cyclization of Tryptamine-Ynamide