1962 年 82 巻 11 号 p. 1496-1502
The Huang-Minlon reduction of sinomenine gives deoxosinomenine (VIII), together with demethoxydeoxodihydrosinomenine (II) as a byproduct. Reduction of methylsinomenine (XIV) with sodium borohydride gives methylsinomeninol-A (XV) and methylsinomeninol-B (XVI), which were found to be epimers originating in the hydroxyl at 6-position. Catalytic reduction of methylsinomeninol-A (XV) afforded methyldihydrosinomeninol-A (XVII) and demethoxy-methyldihydrosinomeninol-A [(+)-dihydrothebainol-A methyl ether] (XX). From the result of these experiments, direct correlation was established between sinomeninol-A (VI) and dihydrothebainol-A (XXI) with regard to the configuration of their hydroxyl at 6-position.