Synthesis of (+)‐O‐Methylthalibrine by Employing a Stereocontrolled Bischler–Napieralski Reaction and an Electrochemically Generated Diaryl Ether

Abstract

(+)‐O‐Methylthalibrine, a bis(benzylisoquinoline) alkaloid from the roots of the genus Thalictrum, has successfully been synthesized through the electrochemical construction of its diaryl ether core and simultaneous introduction of its two stereogenic centers.

Abstract

An efficient electrochemical four‐step route was developed for the preparation of diaryl ether derivatives by using halogenation and dehalogenation processes in addition to electrochemical phenolic oxidation and reduction reactions. The synthesis of (+)‐O‐methylthalibrine was achieved by employing this strategy along with a stereoselective Bischler–Napieralski reaction.