1: 88 percent / OsO4; NMMO / 2-methyl-propan-2-ol; acetone; H2O 2: NaIO4; RuCl3*H2O / CCl4; acetonitrile; H2O / 6 h 3: (COCl)2 / dimethylformamide; toluene / 1 h 4: NEt3 / CH2Cl2 5: 100 percent / H2 / Pd/C / ethyl acetate 6: (COCl)2 / toluene; dimethylformamide / 1 h 7: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 8: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 9: NEt3 / CH2Cl2 10: 85 percent / NaN3; 15-crown-6; DMPU View Scheme

1: 88 percent / OsO4; NMMO / 2-methyl-propan-2-ol; acetone; H2O 2: NaIO4; RuCl3*H2O / CCl4; acetonitrile; H2O / 6 h 3: (COCl)2 / dimethylformamide; toluene / 1 h 4: NEt3 / CH2Cl2 5: 100 percent / H2 / Pd/C / ethyl acetate 6: (COCl)2 / toluene; dimethylformamide / 1 h 7: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 8: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 9: NEt3 / CH2Cl2 10: 85 percent / NaN3; 15-crown-6; DMPU 11: 59 percent / 2-OH-pyridine; NEt3 12: H2; aq. HCl / Pd/C / methanol View Scheme

1: 88 percent / OsO4; NMMO / 2-methyl-propan-2-ol; acetone; H2O 2: NaIO4; RuCl3*H2O / CCl4; acetonitrile; H2O / 6 h 3: (COCl)2 / dimethylformamide; toluene / 1 h 4: NEt3 / CH2Cl2 5: 100 percent / H2 / Pd/C / ethyl acetate 6: (COCl)2 / toluene; dimethylformamide / 1 h 7: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 8: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 9: NEt3 / CH2Cl2 10: 85 percent / NaN3; 15-crown-6; DMPU 11: 59 percent / 2-OH-pyridine; NEt3 View Scheme

1.1: sodium periodate; osmium(VIII) oxide / 0 - 20 °C 2.1: dicyclohexyl(trifluoromethylsulfonyloxy)borane; triethylamine / -78 - 0 °C 3.1: dihydrogen peroxide; lithium hydroxide hydrate / tetrahydrofuran; water / 0.25 h 3.2: Acidic aq. solution 4.1: water; lithium hydroxide hydrate / 1,4-dioxane / 120 h / 40 °C 5.1: diphenyl phosphoryl azide; triethylamine / toluene / 0.33 h / 20 °C 6.1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 65 °C 7.1: 1.5 h / 65 °C 8.1: 2-hydroxy-pyridine / tert-butyl methyl ether / 65 °C View Scheme