4,5,6-Trimethoxyindole was synthesised by three independent routes and condensed with hexane-2,5-dione to give 1,4-dimethyl-5,6,7-trimethoxycarbazole. Formylation of the latter gave a mixture including the 3-formyl derivative which was converted into 8,9,10-trimethoxyellipticine by the modified Pomerantz–Fritsch annelation procedure.
M. J. E. Hewlins, A. H. Jackson, Ana-M. Oliveira-Campos and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1981, 2906 DOI: 10.1039/P19810002906
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