caesium carbonate; potassium iodide in N,N-dimethyl-formamide T=20°C; 8 h;

1: KOH / H2O / 3 h / Heating 2: 25 percent / dicyclohexylurea / tetrahydrofuran / 10 h / Heating 3: 92 percent / Cs2CO3; KI / dimethylformamide / 8 h / 20 °C View Scheme

1: 100 percent / sodium borohydride / methanol; CHCl3 / 1 h / 0 °C 2: 81 percent / TFA; triethylsilane / CH2Cl2 / 0.25 h / 0 °C View Scheme

1: 100 percent / sodium borohydride / methanol; CHCl3 / 1 h / 0 °C 2: 81 percent / TFA; triethylsilane / CH2Cl2 / 0.25 h / 0 °C 3: 73 percent / MgBr2*OEt2 / toluene; diethyl ether / Heating View Scheme

1: 100 percent / sodium borohydride / methanol; CHCl3 / 1 h / 0 °C 2: 81 percent / TFA; triethylsilane / CH2Cl2 / 0.25 h / 0 °C 3: 73 percent / MgBr2*OEt2 / toluene; diethyl ether / Heating 4: 91 percent / K2CO3 / acetone / 8 h / Heating 5: 100 percent / hydrogen / Pd/C / methanol; ethyl acetate / atmospheric pressure View Scheme

1: 100 percent / sodium borohydride / methanol; CHCl3 / 1 h / 0 °C 2: 81 percent / TFA; triethylsilane / CH2Cl2 / 0.25 h / 0 °C 3: 73 percent / MgBr2*OEt2 / toluene; diethyl ether / Heating 4: 91 percent / K2CO3 / acetone / 8 h / Heating 5: 100 percent / hydrogen / Pd/C / methanol; ethyl acetate / atmospheric pressure 6: 52 percent / bromine; glacial AcOH; NaOAc*3H2O / 0.5 h / 20 °C View Scheme