YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Studies on the Alkaloids of Menispermaceous Plants. XCIV
On the Structure of Biscoclaurine Alkaloids. (10). Cleavage of Dauricine by Metallic Sodium in Liquid Ammonia
犬伏 康夫丹羽 英夫
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1952 年 72 巻 6 号 p. 762-765

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The authors obtained from Menispermum dauricum DC. growing in Japan, dauricine and a new base, m. p. 147-150°, which crystallized in yellow needles, but the content of the latter was very minute. The authors carried out the cleavage reaction of O-methyldauricine (II) by metallic sodium in liquid ammonia, and as a result of the investigation of the bisected bases, obtained l-1-(4′-methoxybenzyl)-6, 7-dimethoxy-N-methyl-1, 2, 3, 4-tetrahydroisoquinoline (III) and l-1-(4′-hydroxybenzyl)-6, 7-dimethoxy-N-methyl-1, 2, 3, 4-tetrahydroisoquinoline (l-armepavine) (IV). Thus, it has been proved that dauricine is represented by the formula (I), and the configuration of the two asymmetric centers in the molecule of dauricine are both in l-form.
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© by the PHARMACEUTICAL SOCIETY OF JAPAN
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