Organic reactions in aqueous solution at room temperature. Part IV. In vitro oxidation of a benzylisoquinoline alkaloid to an aporphine alkaloid

Abstract

The benzylisoquinoline derivative, 4',6-00-dimethyl-laudanosoline [ (*)-reticuline] has been synthesised in improved yield, and oxidised under mild aqueous conditions with ferricyanide a t pH 6 to (*)-isoboldine in 5-6s yield. The relevance of this to biogenetic theory is discussed.THE possibility that alkaloids of the aporphine and morphine types might arise in nature by the oxidative coupling of the two aromatic nuclei of suitable benzylisoquinoline alkaloids was first put forward in 1925 by Robins0n.l Independent attempts by Robinson and Schopf 3 to verify it experimentally for the aporphine