Organic Chemistry

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

Authors

Abstract

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

Content

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Supplementary material

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Divergent Total Syntheses of Aspidospermidine, N-Methylaspidospermidine, N-Acetylaspidospermidine and Aspido-spermine via a Tandem Cyclization of Tryptamine-Ynamide
supporting information for the manuscript entitled "Divergent Total Syntheses of Aspidospermidine, N-Methylaspidospermidine, N-Acetylaspidospermidine and Aspido-spermine via a Tandem Cyclization of Tryptamine-Ynamide"