Pakistanamine A Proaporphine-Benzylisoquinoline Dimer

Two approaches to the synthesis of racemic pakistanamine, the only known proaporphine-benzylisoquinoline dimer/ have been published, the full details of which are not available at time of publication. 

Kametani s group subjected a mixture of berbamunines to ferricyanide oxidation to furnish the phenolic proaporphine-benzylisoquinolines 1. Diazomethane methylation then afforded a compound similar to pakistanamine.  

In the second approach, 8-bromodauricine (2), prepared by a six-step sequence from ( )-iV,0-dimethylcoclaurine, was photolyzed in refluxing liquid ammonia containing potassium r-butoxide to produce directly a mixture of pakistanamines.  

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