A highly stereoselective synthesis of (±)-dihydrofumariline-1

Article abstract of DOI:10.1016/S0040-4039(00)61964-0

Stereoselective sodium borohydride reduction of the 8,14-cycloberbine (9) derived from the protoberberine (7), followed by reductive cleavage of C₈-N bond of the resulting 13-hydroxy-8, 14-cycloberbine (10) with sodium cyanoborohydride afforded the spirobenzylisoquinoline (12), N-methylation of which via the oxazolidine (13) provided (±)-dihydrofumariline-l (1).