The structure and absolute stereochemistry of androcymbine (3) are proved by spectroscopic study and by reductive cleavage of its O-methyl ether to a 1-phenethylisoquinoline, which is synthesised. Emphasis is given (a) to the importance of O-methylandrocymbine in relation to colchicine biosynthesis and (b) to the status of androcymbine as the forerunner of a new class of 1-phenethylisoquinoline alkaloids.
A. R. Battersby, R. B. Herbert, L. Pijewska, F. Šantavý and P. Sedmera, J. Chem. Soc., Perkin Trans. 1, 1972, 1736 DOI: 10.1039/P19720001736
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