Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Phenol Oxidation of Isoquinoline Alkaloids. III. Oixdative Coupling of dl-4'-O-Methyl-N-methylcoclaurine
富田 真雄正木 幸雄冨士谷 憲徳坂谷 芳郎
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1968 年 16 巻 4 号 p. 688-694

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Potassium ferricyanide oxidation of dl-4'-O-methyl-N-methylcoclaurine (VII) afforded two species of diphenyl ether derivatives (Base A'and Base B'), which were racemic and diastereoisomeric each to each. The yield was about 15%. Spectrometric studies of the dimerization product and their O-methyl ethers gave proof to their structures. The structures were confirmed by a synthesis of their O-methyl ethers via an alternative route. Configurations of the products were also assigned by the chemical correlation with fangchinoline, having (L, L)-configuration on the two asymmetric carbon atoms.
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© The Pharmaceutical Society of Japan
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