Synthesis of Homoprotoberberines and 8-Oxoprotoberberines by Sequential Bicyclization of Phenylacetamides

Add time:07/23/2019    Source:sciencedirect.com

The reaction of phenylacetamides with oxalyl chloride/Lewis acid provides a convergent, high-yield entry to C-homoprotoberberine and 8-oxoprotoberberine alkaloids from available starting materials. This approach was used to synthesize 8-oxopseudopalmatine starting from N-[β-(3′,4′-dimethoxyphenyl)ethyl]-3,4-dimethoxyphenylacetamide. Some C-homoprotoberberines exhibit significant cytotoxicity against human breast carcinoma cells.

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