Studies on the syntheses of heterocyclic compounds. Part 683. Stevens rearrangement of berbine methiodides by sodium bis-(2-methoxyethoxy)aluminium hydride

Abstract

Refluxing berbine methiodides with sodium bis-(2-methoxyethoxy)aluminium hydride in dioxan resulted in Stevens rearrangements to afford spirobenzylisoquinolines and 8-methylberbines. The stereochemistry at the migrating carbon atom and the relationship between the configuration of the starting quinolizidinium salts and the products have been studied.