hydrogen; palladium dihydroxide in ethanol T=20°C; P=5171.62 Torr; 72 h;

With  osmium(VIII) oxide; 4-methylmorpholine N-oxide in  acetone; tert-butyl alcohol Upjohn dihyroxylation; 24 h;   

Multi-step reaction with 8 steps 1: DMAP / CH2Cl2 / -78 °C2: Pd2(DBA)3*CHCl3; triphenylphosphine / CH2Cl2 / 0 - 20 °C3: NaBH4 / CH2Cl2; methanol / -78 °C4: pyridine; DMAP / CH2Cl2 / 20 °C5: TMSN3 / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 50 °C6: TBAF / tetrahydrofuran / 20 °C7: triethylamine / CH2Cl2 8: N-methylmorpholine N-oxide; water / OsO4 / 2-methyl-propan-2-ol; acetone  

Multi-step reaction with 2 steps 1: triethylamine / CH2Cl2 2: N-methylmorpholine N-oxide; water / OsO4 / 2-methyl-propan-2-ol; acetone  

Multi-step reaction with 7 steps 1: Pd2(DBA)3*CHCl3; triphenylphosphine / CH2Cl2 / 0 - 20 °C2: NaBH4 / CH2Cl2; methanol / -78 °C3: pyridine; DMAP / CH2Cl2 / 20 °C4: TMSN3 / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 50 °C5: TBAF / tetrahydrofuran / 20 °C6: triethylamine / CH2Cl2 7: N-methylmorpholine N-oxide; water / OsO4 / 2-methyl-propan-2-ol; acetone  

Multi-step reaction with 6 steps 1: NaBH4 / CH2Cl2; methanol / -78 °C2: pyridine; DMAP / CH2Cl2 / 20 °C3: TMSN3 / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 50 °C4: TBAF / tetrahydrofuran / 20 °C5: triethylamine / CH2Cl2 6: N-methylmorpholine N-oxide; water / OsO4 / 2-methyl-propan-2-ol; acetone  

Multi-step reaction with 3 steps 1: TBAF / tetrahydrofuran / 20 °C2: triethylamine / CH2Cl2 3: N-methylmorpholine N-oxide; water / OsO4 / 2-methyl-propan-2-ol; acetone  

Multi-step reaction with 4 steps 1: TMSN3 / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 50 °C2: TBAF / tetrahydrofuran / 20 °C3: triethylamine / CH2Cl2 4: N-methylmorpholine N-oxide; water / OsO4 / 2-methyl-propan-2-ol; acetone