Bisbenzylisoquinoline Alkaloids and Related Compounds. Part XII. Synthesis of Stereoisomeric Mixture of Cuspidaline (Studies on the Syntheses of Heterocyclic Compounds. CCXXIX)
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概要
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Bischler-Napieralski reaction of the diamide (IX), which was obtained by Schotten-Baumann reaction of 4-hydroxy-3-methoxyphenethylamine (V) with the acid chloride (VII), gave the dihydroisoquinoline derivative (X), which was converted into the dimethiodide (XI). Reduction with sodium borohydride of the above dimethiodide, followed by hydrolysis with an ethanolic sodium hydroxide solution, afforded the stereoisomeric mixture of cuspidaline (I), mp 110° (sinters at 85°), which was also characterized as its O, O-dimethylcuspidaline (XIII), namely, O-methyldauricine. Furthermore, the attempt to obtain the quarternary salt of II and/or III by phenolic oxidative coupling of the dimethiodide (XIV) of I was examined, but resulted in failure.
- 公益社団法人日本薬学会の論文
- 1968-05-25
著者
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亀谷 哲治
Pharmaceutical Institute, Tohoku University School of Medicine
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佐藤 文夫
Pharmaceutical Institute, Tohoku University
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亀谷 哲治
Pharmaceutical Institute Medical Faculty University Of Osaka
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