Studies on the Alkaloids of Menispermaceous Plants. CCXXIV : Syntheses of Dauricine Type Bases. (1) : Synthesis of 2-Hydroxy-5, 4'-bis(2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetra-hydroisoquinolin-1-ylmethyl)-diphenyl Ether

Abstract

dl-Armepavine (VIIIa) and dl-3'-bromo-4'-O-acetylarmepavine (IX) were synthesized and they were submitted to the Ullmann condensation in pyridine, in the presence of potassium carbonate, with copper powder or copper oxide powder as a catalyst, affording the title compound, 2-hydroxy-5, 4'-bis(2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinolin-1-yl-methyl)diphenyl ether (I). Examination of the infrared and NMR spectra of I indicated that I is a diastereoisomeric racemates having the same planar structure as natural dauri-cine (D, D).