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Updated: May 26, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
A Copper-Catalyzed Decarboxylative Olefination Cascade Enables Access to Protoberberine Alkaloid Frameworks
Ashok R Gudipally1,2, Wayne W Harding1,2,3
1Department of Chemistry, Hunter College, New York, USA.
None:
We describe a streamlined one-pot strategy to construct highly functionalized protoberberine frameworks through a tandem Mannich/intramolecular acylation and copper-promoted decarboxylative olefination sequence. This operationally straightforward process delivers a wide array of derivatives in consistently high yields. Mechanistic investigations, including isolation of key intermediates, support a radical-driven decarboxylative olefination pathway that develops complex protoberberine-type alkaloids with exceptional efficiency. The utility of this synthetic platform is demonstrated through concise total syntheses of the neuroactive tetrahydroprotoberberine alkaloids (±)-isocorypalmine and (±)-stepholidine. Collectively, this chemistry establishes a concise and practical avenue for accessing valuable protoberberine scaffolds from readily available precursors.
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