Protoberberine型アルカロイドの反応(第10報)Acetoneberberine-KMnO_4酸化生成物の構造その2

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Two types of products, 8-acetonyl-2,3-methylenedioxy-9,10-dimethoxy-13-oxido-5,6-dihydrobenz [α] acridizinium (IV) and 2-acetyl-3-hydroxy-4,5-dimethoxyindenone-1 (V), in addition to II and III, were isolated from the oxidation of acetoneberberine (I) with KMnO_4. They were characterized from spectroscopic data and chemical transformations. Refluxing of TV with 10% HCl did not remove the acetonyl group. Reduction of IV with NaBH_4 afforded 8-(2-hydroxypropyl)-13-hydroxytetrahydroberberine (VIII) and 8-(2-hydroxypropyl)-13-oxidoberberinium (IX), while reduction with zinc dust in aqueous acetic acid led to the concurrent elimination of the acetony1 group to form tetrahydroberberine (X) and 13-β-hydroxytetrahydroberberine (dl-ophiocarpine) (XI).
公益社団法人日本薬学会の論文
1975-10-25