Condensation of tryptamine with an indoloquinolizidine precursor gives a keto-amide which cyclises stereoselectively to yield the octacyclic ring structure of the Roxburghines.
H. Riesner and E. Winterfeldt, J. Chem. Soc., Chem. Commun., 1972, 786 DOI: 10.1039/C39720000786
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