potassium hydroxide in ethanol; water 2.8 h; Inert atmosphereReflux;

1.1: 3,4,5-trimethoxyphenylboronic acid / toluene / 1 h / |Reflux; |Dean-Stark 1.2: 46 h / 100 °C / |Molecular sieve; |Sealed tube 1.3: 2 h / |Reflux 2.1: potassium carbonate / acetone / 4 h / |Reflux 3.1: ethanol / 14 h / |Reflux 4.1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 5.1: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 6.1: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 7.1: water; sodium hydroxide / ethanol / 3 h / 20 °C 8.1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 9.1: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C View Scheme

1.1: 3,4,5-trimethoxyphenylboronic acid / toluene / 1 h / |Reflux; |Dean-Stark 1.2: 46 h / 100 °C / |Molecular sieve; |Sealed tube 1.3: 2 h / |Reflux 2.1: potassium carbonate / acetone / 4 h / |Reflux 3.1: ethanol / 14 h / |Reflux 4.1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 5.1: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 6.1: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 7.1: water; sodium hydroxide / ethanol / 3 h / 20 °C 8.1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 9.1: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 10.1: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme

1.1: sodium iodide; potassium hydroxide / ethanol / 90 °C 1.2: 16 h / 100 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / chloroform / 0 - 20 °C 4.1: trichlorophosphate / acetonitrile / 3 h / Reflux; Inert atmosphere 4.2: 20 °C / Inert atmosphere; Cooling with ice 5.1: palladium 10 on activated carbon; hydrogen; acetic acid / methanol / 16 h 6.1: berberine bridge enzyme; tris(hydroxymethyl)methylamine hydrochloride; magnesium chloride / toluene / 24 h / 40 °C / pH 9 / Darkness; Enzymatic reaction View Scheme

1: 90.4 percent / Heating 2: POCl3 / acetonitrile / Heating 3: NaBH4 View Scheme

1: With caesium carbonate in acetone T=65°C; 3.5 h; 2: With lithium hydroxide; water in tetrahydrofuran T=70°C; 2.5 h; 3: With hydrogenchloride in water

acetic anhydride; triethylamine T=110°C; Perkin reaction; 6 h; Inert atmosphere;

1: 48 percent / 1.) benzeneboronic acid / benzene / 96 h / Heating 2: 90 percent View Scheme

1.1: sodium iodide; potassium hydroxide / ethanol / 90 °C 1.2: 16 h / 100 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 20 °C / Inert atmosphere View Scheme

1.1: sodium iodide; potassium hydroxide / ethanol / 90 °C 1.2: 16 h / 100 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / chloroform / 0 - 20 °C 4.1: trichlorophosphate / acetonitrile / 3 h / Reflux; Inert atmosphere 4.2: 20 °C / Inert atmosphere; Cooling with ice 5.1: palladium 10 on activated carbon; hydrogen; acetic acid / methanol / 16 h 6.1: berberine bridge enzyme; tris(hydroxymethyl)methylamine hydrochloride; magnesium chloride / toluene / 24 h / 40 °C / pH 9 / Darkness; Enzymatic reaction View Scheme