Hasubanonine, m.p. 116°, C
21H
27O
5N=C
16H
12O(OCH
3)
4⋅NCH
3, one of the alkaloids of
Stephania japonica MIERS (family Menispermaceae. Japanese name “Hasunohakazura”), forms acetylhasubanol, C
19H
18O
5, by the Hofmann degradation followed by acetolysis, and hydrolysis of the acetylhasubanol gives hasubanol, C
17H
16O
4, which is positive to the Gibbs reagent and forms methylhasubanol, C
18H
18O
4, on methylation. Methyl-hasubanol was confirmed as 3, 4, 6, 8-tetramethoxyphenanthrene (III) by synthesis. Since hasubanol is positive to the Gibbs reagent, Satomi assumed it to be 3, 4, 6-trimethoxy-8-hydroxyphenanthrene.
In the present series of work, hasubanol was derived to ethylhasubanol, which was proved to be 3, 4, 8-trimethoxy-6-ethoxyphenanthrene (VI) by its synthesis. It follows, therefore, that hasubanol is not II but is 3, 4, 8-trimethoxy-6-phenanthrenol (VII).
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