Phenol oxidation. Part II. Synthesis of orientalinone, corydine, and isocorytuberine
Abstract
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.