1: N-bromosuccinimide, (PhCO)2O2 / CCl4 / Heating; Irradiation 2: ethanol; H2O / Heating 3: conc. H2SO4, AcOH, H2O / 80 °C View Scheme

PPA T=100°C; 1 h;

potassium phosphate in toluene T=110°C; 2 h; Schlenk techniqueInert atmosphereGreen chemistry;

bis-triphenylphosphine-palladium(II) chloride; potassium carbonate in N,N-dimethyl-formamide T=130°C; 12 h; Inert atmosphere;

cesium fluoride in acetonitrile T=20°C; 15 h;

tert.-butylhydroperoxide; tetrabutylammomium bromide in water T=120°C; 24 h; Schlenk techniqueSealed tube;

1: 9,9-Dimethoxyxanthene With tert.-butyl lithium in hexane; (+/-)-Tetrahydropapaveroline T=-40 - -30°C; 0.533333 h; Inert atmosphere; 2: methyl iodide in hexane; (+/-)-Tetrahydropapaveroline T=-50 - 20°C; Inert atmosphere; 3: With hydrogenchloride; water in methanol; hexane; (+/-)-Tetrahydropapaveroline pH=3; Inert atmosphere; regioselective reaction;

1: Cs2CO3; tris[2-(2-methoxyethoxy)ethyl]amine; CuCl / dioxane / 20 h / Heating 2: sulfuric acid / 1 h / 85 °C View Scheme

1: Cs2CO3; tris[2-(2-methoxyethoxy)ethyl]amine; CuCl / dioxane / 20 h / Heating 2: sulfuric acid / 1 h / 85 °C View Scheme

1: 9,9-Dimethoxyxanthene With n-butyllithium in (+/-)-Tetrahydropapaveroline T=-13 - -10°C; 2: methylation agent in (+/-)-Tetrahydropapaveroline 3: Acidic aq. solution;