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-OO-dimethyl-laudanosoline [(±)-reticuline] has been synthesised in improved yield, and oxidised under mild aqueous conditions with ferricyanide at pH 6 to (±)-isoboldine in 5–6% yield. The relevance of this to biogenetic theory is discussed.