The divergent 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-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.
An efficient gold(I)-catalyzed intramolecular alkoxylation/double aldol condensation cascade cyclization strategy to synthesize 2,2'-spirobi[indene] derivatives has been developed. The scope of this strategy was examined by using a batch of synthetic alkynone substrates and a possible mechanism was proposed.
Over the past two decades, synthetic strategies for synthesizing
the skeletons of various indole alkaloids based on tryptamine-ynamide
have been continuously developed and applied to the total syntheses
or formal total syntheses of related molecules. In this synopsis,
we summarized the cyclization pathways of tryptamine-ynamide under
different catalytic conditions, emphasizing the reaction mechanism
and applications in the syntheses of indole alkaloids.
The divergent 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-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.
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