Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Utilization of Protopine and Related Alkaloids. VI. Transformation of Berberine to 10b-Methylhexahydrobenzo [c] phenanthridine Derivative
恩田 政行湯浅 久美子岡田 順子片岡 京子阿部 薫
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1973 年 21 巻 6 号 p. 1333-1337

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The methine base (X) derived from berberine chloride via several steps is photocyclized to the two isomeric carbinolamine forms (XI and XII) of 10b-methyl-4b, 10b, 11, 12-tetrahydrochelerythrine. Spectral data and chemical evidences reveal that the positions of the hydroxyl groups are C-6 in XI and C-4b in XII. The cis B/C ring juncture in XI is determined by observation of the nuclear Overhauser effect between 10b-Me and 4b-H. The formation pathways of XI and XII are examined and deduced to be the photoinduced intramolecular alkylation on carbon in the enamine system with olefin.
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© The Pharmaceutical Society of Japan
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