Canadine (4) has been synthesised by methylation of nandinine (3), prepared from 1,2,3,4-tetrahydro-1-(3-hydroxy-4-methoxybenzyl)-6,7-methylenedioxyisoquinoline (13) by a Mannich reaction. This Mannich reaction was studied under various conditions and the structure of an abnormal product, 9-hydroxy-12-hydroxymethyl-10-methoxy-2,3-methylenedioxyberbine, (7) has been elucidated.
T. Kametani, K. Fukumoto, T. Terui, K. Yamaki and E. Taguchi, J. Chem. Soc. C, 1971, 2709 DOI: 10.1039/J39710002709
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