Phenolic oxidative coupling of (±)-N-methylcoclaurine with potassium ferricyanide afforded (±)-glaziovine (III), whose methylation with diazomethane gave (±)-pronuciferine (VI). A very interesting dimeric compound (VIII) was also obtained.
T. Kametani and H. Yagi, J. Chem. Soc. C, 1967, 2182 DOI: 10.1039/J39670002182
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