Reduction-Oxydation of Berbine N-Oxides with Aerated Sodium in Liquid Ammonia

Article abstract of DOI:10.1021/jo00320a031

Reduction-oxidation of trans- or cis-canadine N-oxide (3 or 12) in aerated sodium in liquid ammonia yields nitrone 4 and a little of amine 5.Photolysis of 4 in methanol gives rise to amide 8, lactam 9, and methyl ether 10.Attempted reduction-oxidation of either trans- or cis-xylopinine N-oxides (14 or 15) furnishes only amine 16.The two N-oxides of nandinine (20) proved to be only sparingly soluble in the reaction medium and thus provided only limited yields of nitrone 23.The yield of nitrone is also curtailed if a methyl group is present at C-13 of the starting berbine N-oxide.