Oxidation of 1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxyphenethyl)-6-methoxy-2-methylisoquinoline (III) with potassium ferricyanide or ferric chloride afforded a homoproaporphine (XIII) in good yield by coupling the 8-position of the isoquinoline to the 1-position of the phenethyl group. The syntheses of (III) and its 1-(3-hydroxy-4,5-dimethoxyphenethyl) analogue (IV) are also described.
T. Kametani, H. Yagi, F. Satoh and K. Fukumoto, J. Chem. Soc. C, 1968, 271 DOI: 10.1039/J39680000271
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