1957 Volume 77 Issue 10 Pages 1075-1078
A new phenolic base of m. p. 190-191° was isolated from Berberis amurensis RUPR. var. japonica (REGEL) REHD. forma Bretschneideri (REHD.) OHWI (Japanese name “Akajikuhebinoborazu”) and it was named berbamunine. Its molecular and rational formulae are indicated by C36H40O6N2=C32H25(OCH3)2 (OH)3 (-O-)(NCH3)2. Permanganate oxidation of the O-methyl ether of this base afforded 2-methoxydiphenyl ether-5, 4′-dicarboxylic acid (I) and the methine base obtained by the Hofmann degradation of the O-methyl ether methiodide was found to be identical with O-methyldauricine methyl ether. Consequently, it was clarified that this berbamunine is a phenolic base belonging to the dauricine type, of the biscoclaurine-type bases and that O-methylberbamunine, O-methyldauricine, and O-methylmagnoline are optical isomers indicated by the same structural formula (VI).
