The Journal of Organic Chemistry

Conversion of berberine into phthalideisoquinolines

JL Moniot, M Shamma

文献索引：Moniot,J.L.; Shamma,M. Journal of Organic Chemistry, 1979 , vol. 44, p. 4337 - 4342

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被引用次数: 24

摘要

Ferricyanide oxidation of berberine (1) yields the dimer oxybis (berberine) whose breakdown with methanolic hydrogen chloride gives 8-methoxyberberinephenolbetaine (12). Hydration of 12 in wet ether furnishes enaminol 14 which can be N-methylated to dehydrohydrastine methyl ester (15). NaBH4 reduction of 15 leads to a 1: 2 mixture of (f)-a- hydrastine (9) and (&)-@-hydrastine (6), thus achieving the first conversion of 1 to the ...