1: 52 percent / Et3N / CH2Cl2 / 4 h / 0 °C 2: Jones' reagent / acetone / 3 h / 0 °C View Scheme

in dichloromethane 12 h; Ambient temperature;

triethylamine in tetrahydrofuran; 1,4-dioxane

potassium carbonate in ethanol T=20°C; 96 h;

1: 85 percent / Et3N / CH2Cl2 / 1.17 h / Ambient temperature 2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, 5 min 3: 96 percent / tetrahydrofuran / 0.08 h / -30 °C 4: DOWEX 50W-X8 resin / methanol / 14 h / Ambient temperature 5: tetrahydrofuran / 14 h / Ambient temperature 6: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature 7: 1.) Sudan III, O3, 2.) CH3COOH, Zn / 1.) CH2Cl2, MeOH, -78 deg C, 45 min, 2.) CH2Cl2, MeOH, H2O, -45 deg C, 5 min 8: 1.) dibutylboron triflate, diisopropylethylamine, 3.) 30percent aq. H2O2 9: 1.) diisopropylethylamine, dibutylboron triflate, 2.) lithium borohydride, 3.) 30percent aq. H2O2 10: 1.) camphorsulfonic acid, 2.) acetone / 1.) CH2Cl2, RT, 45 min, 2.) CH2Cl2, RT, overnight 11: 91 percent / periodic acid, RuCl3*3H2O / acetonitrile; CCl4; H2O / 2 h / Ambient temperature 12: Et3N, diethylphosphoryl cyanide / CH2Cl2 / 2 h / Ambient temperature 13: acetyl chloride / methanol / 14 h / Ambient temperature 14: Et3N, diethylphosphoryl cyanide / CH2Cl2 / 14 h 15: trifluoroacetic acid / CH2Cl2 / 0.5 h / Ambient temperature 16: Et3N, diethylphosphoryl cyanide / CH2Cl2 / 14 h 17: 1-hydroxybenzotriazole / methanol / 14 h / Ambient temperature View Scheme

caesium carbonate in dimethylsulfoxide-d6 T=25 - 150°C; P=2280.15 Torr; 24 h; Schlenk techniqueAutoclave;

1: (1S)-1-(hydroxymethyl)-3-methylbutylamine in acetonitrile T=20°C; Electrolysis; 2: carbon dioxide 1 h; 3: p-toluenesulfonyl chloride T=20°C;

triethylamine in dichloromethane T=4 - 20°C; Inert atmosphere;

potassium carbonate

1: 92 percent / Et3N / CH2Cl2 / 1) 0 deg C, 1 h, 2) room temperature, 4 h 2: 1) TsCl, Et3N, DMAP, 2) NaH / 1) CH2Cl2, 0 deg C to room temperature, overnight, 2) THF, 0 deg C to room temperature; room temperature, 24 h 3: 84 percent / CuBr*SEt2 / tetrahydrofuran / 1) -40 deg C to room temperature, 10 min, 2) reflux, 4 h View Scheme