Oxidative transformations in the aporphine alkaloid series

摘要: Abstract Oxidation of the non-phenolic aporphines nuciferine ( 1 ), dicentrine 3 ocopodine 4 ) and thalicarpine 7 by iodine affords corresponding dehydroaporphines 2, 5, 6 8 ). In contrast. oxidation noraporphines proceeds all way to oxoaporphine stage: thus. O-methylnandigerine 9 nordicentrine 11 ovigerine 12 yield oxoaporphines 10, 13 14 The phenolic aporphine N-methylnandigerine 19 is converted in low blue 10,11- o -quinone 20 ; formed as major product mercuric chloride both its 10,11-isomer bulbocapnine 21 dehydronuciferine 2 dehydrodicentrine 5 are oxidized oxygen at pH give 23 ); also rapidly peracetic acid or benzoyl peroxide, benzoate ester 24 being an intermediate latter reaction.