Lanthanum nitrate hexahydrate T=20°C; 0.25 h;

Ambient temperature;

1: 84 percent / pyridine / CH2Cl2 / 16 h / Ambient temperature 2: 46 percent / I2, 1,2-bis(diphenylphosphino)ethane / CH2Cl2 / 4 h / Ambient temperature 3: 34 percent / dimethylsulfoxide / 2 h / Ambient temperature 4: 79 percent / trifluoroacetic acid, H2O / CH2Cl2 5: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, 0 deg C, 1.5 h 6: 88 percent / H2 / 10percent Pd/C / diethyl ether / 16 h 7: 44 percent / molecular sieves 4 A, pyridinum dichromate / dimethylformamide / 120 h / Ambient temperature 8: 94 percent / 10percent aq. tetrabutylammonium hydroxide / CH2Cl2 / 16 h View Scheme

1.1: (COCl)2; DMSO; Et3N / dimethylsulfoxide; CH2Cl2 / -78 - 25 °C 2.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 1 h / 0 °C 2.2: tetrahydrofuran; hexane / 0 °C 3.1: PTSA / methanol / 1 h / 20 °C 4.1: Jones reagent / acetone / 0 - 20 °C 5.1: 60 percent / Li; liq. NH3 / tetrahydrofuran / 2 h / cooling View Scheme

triphenylphosphine; diethylazodicarboxylate; methyl iodide in toluene Iodination;

1: CrO3, pyridine, HCl 3: p-TsOH / methanol 4: H2 / Pd/C 5: CrO3, pyridine, HCl View Scheme

1: 81 percent / pyridinium chlorochromate / CH2Cl2 / Ambient temperature 2: 100 percent / 4 Angstroem molecular sieves / benzene / 3 h / Heating 3: 74 percent / tetrahydrofuran / -110 to -80 deg C 4: NaIO4 / methanol; H2O; tetrahydrofuran / 3 h / Ambient temperature View Scheme

triethylamine in dichloromethane 1 h;

1: 84 percent / pyridine / CH2Cl2 / 16 h / Ambient temperature 2: 46 percent / I2, 1,2-bis(diphenylphosphino)ethane / CH2Cl2 / 4 h / Ambient temperature 3: 34 percent / dimethylsulfoxide / 2 h / Ambient temperature View Scheme