The total synthesis of the antibiotic bikaverin (1) is described, from orcinol and 3-(2,4,5-trimethoxyphenyl)propiononitrile. The intermediate 6-hydroxy-3,7,8,10-tetramethoxy-1-methylbenzo[b]xanthen-12-one is oxidised to the 6,11-quinone (20), which is demethylated, preferably with iodide ion, to give bikaverin (1).
D. H. R. Barton, L. Cottier, K. Freund, F. Luini, P. D. Magnus and I. Salazar, J. Chem. Soc., Perkin Trans. 1, 1976, 499 DOI: 10.1039/P19760000499
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