Ferricyanide oxidation of 1,2,3,4-tetrahydro-7-hydroxy-1-(2-hydroxy-4,5-dimethoxybenzyl)-6-methoxy-2-methyl-isoquinoline afforded a mixture of two dienones in 26% yield. Borohydride reduction of one of these gave the corresponding dienol which rearranged in acidic media to give either orientalinone, corydine, or isocorytuberine depending on the conditions used.
A. H. Jackson and J. A. Martin, J. Chem. Soc. C, 1966, 2222 DOI: 10.1039/J39660002222
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