Mannich reaction of 1 -(2-bromo-5-hydroxy-4-methoxybenzyl) -1;2,3,4-tetrahydro-6 7-methylenedioxyisoquinoline (1x1 gave 12-bromonandinine (11) which was debrominated to afford (i)-nandinine (I). Methylation of (i)-nandinine with diazomethane gave (i) -canadine (111). dehydrogenation of which with iodine afforded berberine iodide (XI). NANDININE (I), C&,,NO,, and canadine (III), C20H21N0,, have been isolated from Nandirta domestics and CorydaZis 3 species, respectively. Their structures were elucidated from degradative evidence and by total synthesis.** We are investigating a modified Mannich reaction which selectively affords protoberberines cyclised ortho to the hydroxy group. This reaction has been

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