potassium carbonate in N,N-dimethyl-formamide 0.5 h; Ambient temperature;

N-ethyl-N,N-diisopropylamine in dichloromethane 0.75 h; Inert atmosphereCooling with ice;

in tetrahydrofuran; water

1.1: 80 percent / zinc amalgam; HCl / ethanol / 3 h / Heating 2.1: 95 percent / K2CO3 / acetone / 6 h / Heating 3.1: 90 percent / 24 h / 180 °C 4.1: 95 percent / KOH / methanol / 10 h / Heating 5.1: 96 percent / sodium hydroxyde / H2O / 1 h / Heating 6.1: NaHCO3; ozone / methanol; CH2Cl2 / 0.22 h / -70 °C 6.2: 80 percent / dimethyl sulfide / methanol; CH2Cl2 / 8 h / 20 °C 7.1: Mg; iodine / diethyl ether 7.2: 88 percent / diethyl ether / 3 h / 20 °C 8.1: 96 percent / PCC; silica gel / CH2Cl2 / 2 h / 20 °C 9.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.67 h / 20 °C 9.2: tetrahydrofuran; various solvent(s) / 10 h / 20 °C 9.3: 91 percent / tetrahydrofuran; various solvent(s) / 0.5 h / 180 °C 10.1: 90 percent / tetrahydrofuran / 2 h / sonication 11.1: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 12.1: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 13.1: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 14.1: 28 percent / propionic acid / 48 h / 180 °C 15.1: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 16.1: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 17.1: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 18.1: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 19.1: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme

1.1: Et3N / diethyl ether / 2 h / 20 °C 1.2: 71 percent / I2 / H2O; diethyl ether / 0.67 h / 20 °C 2.1: 81 percent / NH2OH*HCl; NaOH / ethanol / 4 h / Heating 3.1: 96 percent / diethyl chlorophosphite / CHCl3 / 2 h / 20 °C View Scheme

T=50°C; Knoevenagel condensation; 1 h;

bromocyane; L-(+)-tartaric acid in methanol T=0 - 20°C; screw cap tube;

sulfuric acid; nitric acid; HNO2

bei maessiger Waerme;

1.1: potassium carbonate / ethanol / 20 h / 20 °C / Inert atmosphere 2.1: ammonium acetate / acetic acid / 5 h / Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere; Reflux 4.1: triethylamine / dichloromethane / 3 h / 20 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux 6.1: sodium hydroxide / chloroform / 0 - 20 °C 7.1: trichlorophosphate / acetonitrile / 3 h / Reflux; Inert atmosphere 7.2: 20 °C / Inert atmosphere; Cooling with ice 8.1: palladium 10 on activated carbon; hydrogen; acetic acid / methanol / 16 h 9.1: berberine bridge enzyme; tris(hydroxymethyl)methylamine hydrochloride; magnesium chloride / toluene / 24 h / 40 °C / pH 9 / Darkness; Enzymatic reaction View Scheme