Synthesis and stereochemistry of tetrahydroprotoberberine derivatives

A series of 5-hydroxytetrahydroprotoberberines has been prepared from 3-aryltetrahydroisoquinoline derivatives via successive N-alkylation, oxidation and cyclization in acidic media. The relative configurations of the resulting diastereomeric 5-hydroxytetrahydroprotoberberines are reported.