Alkaloid biosynthesis. Part XVIII. Biosynthesis of colchicine from the 1-phenethylisoquinoline system

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Abstract
Extensive tracer experiments show that colchicine (9) is formed by a novel biosynthetic pathway from 1,2,3,4-tetrahydro-7-hydroxy-1-(3-hydroxy-4,5-dimethoxyphenethyl)-6-methoxy-2-methylisoquinoline (3)(autumnaline) with O-methylandrocymbine (6) as a key intermediate. The way in which autumnaline is constructed in the living system is also studied.