1: 96 percent / OsO4; NMO / acetone; 2-methyl-propan-2-ol; H2O / 3 h / 0 °C 2: 80 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 3 h / 20 °C View Scheme

1: 96 percent / OsO4; NMO / acetone; 2-methyl-propan-2-ol; H2O / 3 h / 0 °C 2: 86 percent / DMAP; pyridine / CH2Cl2 / 0 °C 3: 86 percent / H2 / Pd/C / tetrahydrofuran; ethanol / -90 - 20 °C View Scheme

1.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C 2.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 3.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C 3.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C 4.1: 62 percent / DBU / toluene / 1 h / 0 °C 5.1: 91 percent / DBU / toluene / 1 h / 0 °C View Scheme