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 7.1: NaBH4 / H2O; acetonitrile / 0.25 h 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