hydrogen; palladium on activated charcoal in methanol; ethyl acetate P=760 Torr; 1 h; Ambient temperature;

osmium(VIII) oxide; 4-methylmorpholine N-oxide in water; acetone; tert-butyl alcohol T=0°C; Upjohn dihydroxylation; 4 h;

ammonium hydroxide in methanol 16 h; Ambient temperature;

1: 85 percent / 80percent AcOH, 2N HCl / H2O / 5 h / 90 °C 2: 90 percent / 2,6-lutidine, KF, 18-crown-6 ether / CH2Cl2 / 0.5 h / Ambient temperature 3: 11 percent / 1.) molecular sieves 4 Angstroem, 2.) BF3*Et2O / CH2Cl2 / 0.33 h / -40 °C 4: 76 percent / H2 / Pd/C / ethyl acetate; methanol / 1 h / 760 Torr / Ambient temperature View Scheme

1: 90 percent / 2,6-lutidine, KF, 18-crown-6 ether / CH2Cl2 / 0.5 h / Ambient temperature 2: 11 percent / 1.) molecular sieves 4 Angstroem, 2.) BF3*Et2O / CH2Cl2 / 0.33 h / -40 °C 3: 76 percent / H2 / Pd/C / ethyl acetate; methanol / 1 h / 760 Torr / Ambient temperature View Scheme

1: KOH / dimethylformamide / 7 h / Ambient temperature 2: 85 percent / 80percent AcOH, 2N HCl / H2O / 5 h / 90 °C 3: 90 percent / 2,6-lutidine, KF, 18-crown-6 ether / CH2Cl2 / 0.5 h / Ambient temperature 4: 11 percent / 1.) molecular sieves 4 Angstroem, 2.) BF3*Et2O / CH2Cl2 / 0.33 h / -40 °C 5: 76 percent / H2 / Pd/C / ethyl acetate; methanol / 1 h / 760 Torr / Ambient temperature View Scheme

1: 18 percent / 1.) molecular sieves 4 Angstroem, 2.) BF3*Et2O / CH2Cl2 / 1.) -30 deg C, 10 min, 2.) -30 deg C, 1 h 2: 76 percent / H2 / Pd/C / ethyl acetate; methanol / 1 h / 760 Torr / Ambient temperature View Scheme

1: 11 percent / 1.) molecular sieves 4 Angstroem, 2.) BF3*Et2O / CH2Cl2 / 0.33 h / -40 °C 2: 76 percent / H2 / Pd/C / ethyl acetate; methanol / 1 h / 760 Torr / Ambient temperature View Scheme

1: 43 percent / 1.) mol. sieves 4 Angstroem, 2.) Me3Si-OTf / CH2Cl2 / 1.) -10 deg C, 10 min, 2.) a.) -10 deg C, 15 min, b.) 0 deg C, 15 min 2: 76 percent / H2 / Pd/C / ethyl acetate; methanol / 1 h / 760 Torr / Ambient temperature View Scheme

1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine / tetrahydrofuran; dichloromethane / 6 h / 0 °C / Inert atmosphere 2: sodium tetrahydroborate; cerium(III) chloride / methanol; dichloromethane / 1 h / -78 °C 3: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 4 h / 0 °C View Scheme