molecular sieve; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide in dichloromethane T=20°C; 0.5 h;

1: CCl4, hexamethylphosphorus triamide / 1) -78 to -40 deg C, 2) -40 deg C, 1 h, 3) to r.t., 1 h 2: 1) NaH / 1) CH3CN, r.t., 1 h, 2) THF, r.t., 12 h 3: TFA / H2O / 0.5 h / Ambient temperature View Scheme

1: 100 percent / tetrahydrofuran / 1 h / -78 - 20 °C 2: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 3: 97 percent / NaIO4 / H2O / 1 h / 20 °C 4: 86 percent / NaH / dimethylsulfoxide; tetrahydrofuran / 3 h / Heating 5: Grubbs catalyst / CH2Cl2 / 4 h / 24 °C 6: pyridinium chlorochromate; 4 Angstroem molecular sieves; acetic acid / CH2Cl2 / 12 h / 20 °C View Scheme

1: CCl4; P(NMe2)3 / 1 h / -78 °C 2: NaH / 24 h / 20 °C 3: 100 percent / TFA 4: 88.7 percent / NH3 / methanol / 22 h / 116 °C View Scheme

1: 91 percent / NaH / tetrahydrofuran; dimethylsulfoxide / 3 h / Heating 2: 75 percent / dicyclohexylcarbodiimide; CF3CO2H; pyridine / DMSO / toluene / 10 h / 20 °C 3: 80 percent / tetrahydrofuran / 1 h / -78 - 20 °C 4: 95 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 5: aq. NaIO4 / 0.58 h / 0 - 20 °C 6: 11.4 g / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 7: Grubbs' catalyst / CH2Cl2 / 4 h / 24 °C 8: 8.3 g / 4 Angstroem molecular sieves; pyridinium dichromate; AcOH / CH2Cl2 / 12 h / 24 °C View Scheme

1: CCl4; P(NMe2)3 / 1 h / -78 °C 2: NaH / 24 h / 20 °C 3: 100 percent / TFA View Scheme

1: CCl4, hexamethylphosphorus triamide / 1) -78 to -40 deg C, 2) -40 deg C, 1 h, 3) to r.t., 1 h 2: 1) NaH / 1) CH3CN, r.t., 1 h, 2) THF, r.t., 12 h 3: 87 percent / TFA / H2O / 0.5 h / Ambient temperature 4: 42 percent / H2 / 10percent Pd/C / ethanol / 2 h / 2327.2 Torr / Ambient temperature View Scheme