sodium methylate in methanol T=60°C; 3 h; Inert atmosphere;

hydrogenchloride; iron in ethanol; water T=80°C; 1.5 h;

1: potassium tert-butylate / dimethyl sulfoxide / 4 h / 100 °C 2: iron; hydrogenchloride / ethanol; water / 1.5 h / 80 °C View Scheme

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 4 h / 150 °C / Sealed tube 2: sodium hydroxide / methanol / 0.5 h / 20 °C 3: palladium 10 on activated carbon; hydrogen / methanol / 2.17 h / 760.05 Torr View Scheme

1: sodium hydroxide / methanol / 0.5 h / 20 °C 2: palladium 10 on activated carbon; hydrogen / methanol / 2.17 h / 760.05 Torr View Scheme

1: water; palladium diacetate / 20 °C / Inert atmosphere 2: 2,6-dimethylpyridine; trifluoroacetic anhydride / toluene / -50 °C / Inert atmosphere; Reflux 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 4 h / 150 °C / Sealed tube 4: sodium hydroxide / methanol / 0.5 h / 20 °C 5: palladium 10 on activated carbon; hydrogen / methanol / 2.17 h / 760.05 Torr View Scheme

1: dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate; potassium phosphate / butan-1-ol; water 2: sodium methylate / methanol View Scheme

tryptophan 7-halogenase (recombinant P. fluorescens BL915); sodium chloride; flavin reductase in phosphate buffer T=30°C; pH=7.2; 16 h; Enzymatic reaction; Further byproducts.;

acetic acid in N,N-dimethyl-formamide T=60°C; 12 h;

1: With magnesium sulfate; trifluoroacetic acid in dichloromethane T=20°C; Pictet-Spengler cyclisation; 18 h; Inert atmosphere; 2: With sodium hydrogencarbonate in methanol; dichloromethane; water pH=9;