文章基本信息

标题：Studies on the Alkaloids of Menispermaceous Plants. CXXII. Structure of Trilobine and Isotrilobine. (12).
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作者：Masao Tomita ; Yasuo Inubushi
期刊名称：Chemical and Pharmaceutical Bulletin
印刷版ISSN：0009-2363
电子版ISSN：1347-5223
出版年度：1955
卷号：3
期号：1
页码：7-11
DOI：10.1248/cpb1953.3.7
出版社：The Pharmaceutical Society of Japan
摘要：In an earlier paper²⁾ of this series, experimental evidence was presented that the methine base obtained by the Hofmann degradation of O-methylanhydrodemethyloxy-acanthine (III), a trilobine-type base derived from oxyacanthine (I, R=H), was identical with trilobine methyl methine or isotrilobine methyl methine. On this basis it was suggested that trilobine and isotrilobine are optical isomers, both having the common structure (III). In the present series of experiments, it was confirmed that although so far trilobine was considered to possess two N-CH₃ groups, actually one of the two nitrogen atoms is present as N-CH₃, and the other, as an NH group (see Table I). It follows, therefore, that isotrilobine should be represented by the structure of (IX, R₁=R₂=CH₃), whereas trilobine by (IX, R₁=H, R₂=CH₃ or R₁=CH₃, R₂=H). Furthermore, it was suggested that the stereochemical arrangments about the two asymmetric centers in these bases are both of (-, +) type.