palladium on activated charcoal; hydrogen in methanol T=20°C;

hydrogen; palladium(II) oxide hydrate in ethanol

hydrogen; palladium on activated charcoal in methanol T=20°C; 40 h;

1.1: Et3N / CH2Cl2 / 1 h / 20 °C 2.1: Jones reagent / acetone / 0.25 h / at ice bath 3.1: tetrahydrofuran / 2 h / -78 - 20 °C 4.1: BF3*Et2O / CH2Cl2 / 0.25 h / 20 °C 5.1: 84 percent / NMO / OsO4 / H2O; tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating 6.1: 94 percent / BF3*Et2O / CH2Cl2 / 0.25 h / 20 °C 7.1: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath 8.1: DCC / tetrahydrofuran / 6 h / Heating 9.1: t-BuOCl / CH2Cl2 / 10 h / 20 °C / Heating; in dark 9.2: Zn(OAc)2 / nitromethane / 1 h / 20 °C 10.1: H2 / 10 percent Pd-C / methanol / 40 h / 20 °C View Scheme

1.1: 94 percent / BF3*Et2O / CH2Cl2 / 0.25 h / 20 °C 2.1: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath 3.1: DCC / tetrahydrofuran / 6 h / Heating 4.1: t-BuOCl / CH2Cl2 / 10 h / 20 °C / Heating; in dark 4.2: Zn(OAc)2 / nitromethane / 1 h / 20 °C 5.1: H2 / 10 percent Pd-C / methanol / 40 h / 20 °C View Scheme

1.1: Jones reagent / acetone / 0.25 h / at ice bath 2.1: tetrahydrofuran / 2 h / -78 - 20 °C 3.1: BF3*Et2O / CH2Cl2 / 0.25 h / 20 °C 4.1: 84 percent / NMO / OsO4 / H2O; tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating 5.1: 94 percent / BF3*Et2O / CH2Cl2 / 0.25 h / 20 °C 6.1: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath 7.1: DCC / tetrahydrofuran / 6 h / Heating 8.1: t-BuOCl / CH2Cl2 / 10 h / 20 °C / Heating; in dark 8.2: Zn(OAc)2 / nitromethane / 1 h / 20 °C 9.1: H2 / 10 percent Pd-C / methanol / 40 h / 20 °C View Scheme

1.1: BF3*Et2O / CH2Cl2 / 0.25 h / 20 °C 2.1: 84 percent / NMO / OsO4 / H2O; tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating 3.1: 94 percent / BF3*Et2O / CH2Cl2 / 0.25 h / 20 °C 4.1: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath 5.1: DCC / tetrahydrofuran / 6 h / Heating 6.1: t-BuOCl / CH2Cl2 / 10 h / 20 °C / Heating; in dark 6.2: Zn(OAc)2 / nitromethane / 1 h / 20 °C 7.1: H2 / 10 percent Pd-C / methanol / 40 h / 20 °C View Scheme

1.1: tetrahydrofuran / 2 h / -78 - 20 °C 2.1: BF3*Et2O / CH2Cl2 / 0.25 h / 20 °C 3.1: 84 percent / NMO / OsO4 / H2O; tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating 4.1: 94 percent / BF3*Et2O / CH2Cl2 / 0.25 h / 20 °C 5.1: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath 6.1: DCC / tetrahydrofuran / 6 h / Heating 7.1: t-BuOCl / CH2Cl2 / 10 h / 20 °C / Heating; in dark 7.2: Zn(OAc)2 / nitromethane / 1 h / 20 °C 8.1: H2 / 10 percent Pd-C / methanol / 40 h / 20 °C View Scheme

1.1: 84 percent / NMO / OsO4 / H2O; tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating 2.1: 94 percent / BF3*Et2O / CH2Cl2 / 0.25 h / 20 °C 3.1: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath 4.1: DCC / tetrahydrofuran / 6 h / Heating 5.1: t-BuOCl / CH2Cl2 / 10 h / 20 °C / Heating; in dark 5.2: Zn(OAc)2 / nitromethane / 1 h / 20 °C 6.1: H2 / 10 percent Pd-C / methanol / 40 h / 20 °C View Scheme

1.1: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath 2.1: DCC / tetrahydrofuran / 6 h / Heating 3.1: t-BuOCl / CH2Cl2 / 10 h / 20 °C / Heating; in dark 3.2: Zn(OAc)2 / nitromethane / 1 h / 20 °C 4.1: H2 / 10 percent Pd-C / methanol / 40 h / 20 °C View Scheme