1: ethanol / 14 h / |Reflux 2: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 3: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 4: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 5: water; sodium hydroxide / ethanol / 3 h / 20 °C 6: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 7: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 8: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme

1: ethanol / 14 h / |Reflux 2: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 3: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 4: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 5: water; sodium hydroxide / ethanol / 3 h / 20 °C 6: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 7: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 8: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme

1: 180 °C / Neat (no solvent) 2: trichlorophosphate / benzene / 80 °C View Scheme

1: 100 percent / 12 h / 20 °C 2: 86 percent / POCl3 / toluene / 1 h / 85 °C View Scheme

sodium hydroxide; ammonia; benzaldehyde in N-methyl-acetamide; methanol; 2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(1,3-bis-nitrooxycyclohexyl-2)-acetamide oxalate; ethanol; dichloromethane; toluene

1: 78 percent / 1 h / Heating 2: BF3*OEt2; BH3*THF / tetrahydrofuran / 2 h / Heating View Scheme

1.1: triethylamine / dichloromethane / 3 h / 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux 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

T=20°C; 12 h;

12 h; Inert atmosphereReflux;