CF3CO3H in dichloromethane T=22°C; 1 h;

potassium hydroxide in methanol 1 h; Heating;

CF3CO3H; trifluoroacetic acid in chloroform 3 h; Ambient temperature;

2: BH3, O2 / tetrahydrofuran / 1.) 0 deg C (1.5 h) , 22 deg C (16 h) 3: 1.) LiCO3, 2.) Jones reagent / 1.) dimethylacetamide, 150 deg C, 15 min 4: OsO4, C5H5N / 3 h / 0 °C 5: 74 percent / CF3CO3H / CH2Cl2 / 1 h / 22 °C View Scheme

1: OsO4, C5H5N / 3 h / 0 °C 2: 74 percent / CF3CO3H / CH2Cl2 / 1 h / 22 °C View Scheme

1: BH3, O2 / tetrahydrofuran / 1.) 0 deg C (1.5 h) , 22 deg C (16 h) 2: 1.) LiCO3, 2.) Jones reagent / 1.) dimethylacetamide, 150 deg C, 15 min 3: OsO4, C5H5N / 3 h / 0 °C 4: 74 percent / CF3CO3H / CH2Cl2 / 1 h / 22 °C View Scheme

1: 1.) LiCO3, 2.) Jones reagent / 1.) dimethylacetamide, 150 deg C, 15 min 2: OsO4, C5H5N / 3 h / 0 °C 3: 74 percent / CF3CO3H / CH2Cl2 / 1 h / 22 °C View Scheme

1: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C 2: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature 3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 6: 96 percent / CSA / 24 h / Ambient temperature 7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating View Scheme

1: 1.) n-BuLi, 2.) 30percent H2O2 / 1.) THF, -78 deg C, 3 h, 2.) acetic acid, room temperature, 15 h 2: 85 percent / Ti(O-iPr)4, (+)-L-diethyl tartrate, cumene hydroperoxide, 4 Angstroem MS / CH2Cl2 / 144 h / -25 °C 3: 82 percent / CuCN / diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 3 h 4: 53 percent / CF3CO3H, CF3CO2H / CHCl3 / 3 h / Ambient temperature View Scheme

1: Br2 / methanol 2: acetone / 18 h / Heating 3: NaH / tetrahydrofuran / 0.5 h / 25 °C 4: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h 5: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 6: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 7: 96 percent / CSA / 24 h / Ambient temperature 8: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 9: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating View Scheme