Utilization of Protopine and Related Alkaloids. XIV. Oxidation of the Photoadduct of 1-Oxoanhydromethylberberine with Nitrosobenzene, and Synthesis of Ring C-Substituted Benzo [c] phenanthridines
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概要
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Oxidation of the photo-adduct (2) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone under anhydrous conditions gives the imine (3) and the aniline (4). The oxidation of 2 in the presence of water and anhydrous methanol affords the 1-oxo-2β, 4β-epoxyimine (6) and the 4bα-methoxy-10bβ, 12β-epoxyimine (8), respectively. The mechanisms of formation of these compounds are discussed. The quinone (5), derived from 3 and 4,is reduced with sodium borohydride to yield the cis-diol (25) and the trans-diol (26). On reduction with lithium aluminum hydride and subsequent hydrogenation over palladiumcarbon, 8 gives the 4bβH-12β-anilino-10bβ-ol (33) and the 4bαH isomer (34).
- 公益社団法人日本薬学会の論文
- 1983-05-25
著者
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恩田 政行
School of Pharmaceutical Sciences, Kitasato University
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山口 裕子
Research Laboratories Yoshitomi Pharmaceutical Industries Ltd.
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恩田 政行
Shenyang Pharmaceutical University
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針谷 義弘
北里大薬
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山口 裕子
School of Pharmaceutical Sciences, Kitasato University
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針谷 義弘
School of Pharmaceutical Sciences, Kitasato University
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