Total synthesis of bikaverin (6,11-dihydroxy-3,8-dimethoxy-1-methylbenzo[b]xanthen-7,10,12-trione)

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TL;DRAbstract

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).

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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).

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