Synthetic Studies on Javaberine A: Construction of the Tetrahydroprotoberberine Framework Based on a Double Hydroamination Strategy

The tetrahydroprotoberberine framework of javaberine A was synthesized by repeated hydroamination of dienylamine as the key step. The selection of the reaction solvents and additives highly influenced the reaction pathway and stereoselectivity, and stepwise hydroamination with optimal reaction conditions effectively constructed the tetrahydroprotoberberine skeleton.