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

1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C 2: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C 3: 96 percent / OsO4; NMO / acetone; 2-methyl-propan-2-ol; H2O / 3 h / 0 °C 4: 80 percent / H2 / Pd/C / tetrahydrofuran; ethanol / 3 h / 20 °C 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: 4-methyl-morpholine; o-nitrobenzenesulfonyl hydrazide; triethylamine / 8 h / 0 - 20 °C / Inert atmosphere View Scheme

1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C 2: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C 3: 96 percent / OsO4; NMO / acetone; 2-methyl-propan-2-ol; H2O / 3 h / 0 °C 4: 86 percent / DMAP; pyridine / CH2Cl2 / 0 °C 5: 86 percent / H2 / Pd/C / tetrahydrofuran; ethanol / -90 - 20 °C View Scheme

1.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C 2.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C 3.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C 4.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 5.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C 5.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C 6.1: 62 percent / DBU / toluene / 1 h / 0 °C 7.1: 91 percent / DBU / toluene / 1 h / 0 °C View Scheme