boron tribromide in dichloromethane T=-20 - 20°C;

NADPH-generating system; rat liver epoxide hydrolase; recombinant human cytochrome P450 1A1 expresseded in E. coli in water T=37°C; Oxidation; pH=7.4; Enzymatic reaction; Further byproducts given. Title compound not separated from byproducts;

1: BF3-Et2O 2: Pd / (heating) View Scheme

phosphoric acid in methanol T=60°C; 5 h; Yield given. Yields of byproduct given;

1.1: sodium hydroxide / ethanol; water / 1 h / Reflux 2.1: methanesulfonic acid / 1 h / 50 °C 3.1: pyridine / dichloromethane / 0.17 h / 20 °C 3.2: -78 - 20 °C 4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 5.1: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C 6.1: platinum (II) chloride / toluene / 80 °C 7.1: boron tribromide View Scheme

1.1: methanesulfonic acid / 1 h / 50 °C 2.1: pyridine / dichloromethane / 0.17 h / 20 °C 2.2: -78 - 20 °C 3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 4.1: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C 5.1: platinum (II) chloride / toluene / 80 °C 6.1: boron tribromide View Scheme

1: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C 2: platinum (II) chloride / toluene / 80 °C 3: boron tribromide View Scheme

1: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / 1,4-dioxane / Reflux 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine 3: methanol; potassium carbonate / tetrahydrofuran 4: platinum (II) chloride 5: boron tribromide View Scheme

1.1: (1,2,3,4,5-pentaphenylferrocen-1'-yl)-di-tert-butylphosphine; bis(dibenzylideneacetone)-palladium(0) / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: sodium hydroxide / ethanol; water / 1 h / Reflux 3.1: methanesulfonic acid / 1 h / 50 °C 4.1: pyridine / dichloromethane / 0.17 h / 20 °C 4.2: -78 - 20 °C 5.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 6.1: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C 7.1: platinum (II) chloride / toluene / 80 °C 8.1: boron tribromide View Scheme

1.1: pyridine / dichloromethane / 0.17 h / 20 °C 1.2: -78 - 20 °C 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 3.1: methanol; potassium carbonate / tetrahydrofuran / 1 h / 20 °C 4.1: platinum (II) chloride / toluene / 80 °C 5.1: boron tribromide View Scheme