1: 50 percent / (COCl)2; DMSO; pyridine / CH2Cl2 / -78 - 20 °C 2: OsO4; NMO / tetrahydrofuran; H2O / 0.5 h 3: 0.783 g / p-TsOH*H2O / 0.33 h 4: 0.232 g / NaBH4 / methanol / 0.5 h 5: H2 / 10 percent Pd/C / methanol / 0.5 h View Scheme

1: OsO4; NMO / tetrahydrofuran; H2O / 0.5 h 2: 0.783 g / p-TsOH*H2O / 0.33 h 3: 0.232 g / NaBH4 / methanol / 0.5 h 4: H2 / 10 percent Pd/C / methanol / 0.5 h View Scheme

1.1: disodium hydrogenphosphate / water / 14 h / 25 - 30 °C / pH 7 / Enzymatic reaction 2.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 25 - 45 °C / Inert atmosphere 2.2: 22 h / 25 - 30 °C / Inert atmosphere 3.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tert-butyl alcohol; acetone / 8 h / 20 - 25 °C 4.1: toluene-4-sulfonic acid / acetone / 4 h / 25 - 30 °C 5.1: hydrazine hydrate / ethanol / 10 h / 60 - 65 °C View Scheme

1.1: potassium dihydrogenphosphate; phosphoric acid / water / 22 h / 25 - 99 °C / pH 4.1 2.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2 h / -70 - -60 °C 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / N,N-dimethyl-formamide / 16 h / 10 - 30 °C / Inert atmosphere 4.1: disodium hydrogenphosphate / water / 14 h / 25 - 30 °C / pH 7 / Enzymatic reaction 5.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 25 - 45 °C / Inert atmosphere 5.2: 22 h / 25 - 30 °C / Inert atmosphere 6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tert-butyl alcohol; acetone / 8 h / 20 - 25 °C 7.1: toluene-4-sulfonic acid / acetone / 4 h / 25 - 30 °C 8.1: hydrazine hydrate / ethanol / 10 h / 60 - 65 °C View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / N,N-dimethyl-formamide / 16 h / 10 - 30 °C / Inert atmosphere 2.1: disodium hydrogenphosphate / water / 14 h / 25 - 30 °C / pH 7 / Enzymatic reaction 3.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 25 - 45 °C / Inert atmosphere 3.2: 22 h / 25 - 30 °C / Inert atmosphere 4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tert-butyl alcohol; acetone / 8 h / 20 - 25 °C 5.1: toluene-4-sulfonic acid / acetone / 4 h / 25 - 30 °C 6.1: hydrazine hydrate / ethanol / 10 h / 60 - 65 °C View Scheme

1.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2 h / -70 - -60 °C 2.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / N,N-dimethyl-formamide / 16 h / 10 - 30 °C / Inert atmosphere 3.1: disodium hydrogenphosphate / water / 14 h / 25 - 30 °C / pH 7 / Enzymatic reaction 4.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 25 - 45 °C / Inert atmosphere 4.2: 22 h / 25 - 30 °C / Inert atmosphere 5.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tert-butyl alcohol; acetone / 8 h / 20 - 25 °C 6.1: toluene-4-sulfonic acid / acetone / 4 h / 25 - 30 °C 7.1: hydrazine hydrate / ethanol / 10 h / 60 - 65 °C View Scheme

1: pyridine / 24 h / 20 °C 2: sodium iodide / butanone / 24 h / 120 °C 3: zinc / ethanol / 1 h / 70 °C 4: sodium carbonate / ethanol / 1 h / 50 °C 5: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 6: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C View Scheme

1: sodium iodide / butanone / 24 h / 120 °C 2: zinc / ethanol / 1 h / 70 °C 3: sodium carbonate / ethanol / 1 h / 50 °C 4: N,N-dimethyl-formamide; toluene / 5 h / 110 °C 5: palladium 10 on activated carbon; hydrogen / methanol / 14 h / 20 °C View Scheme

1: p-toluenesulfonic acid / acetone / 15 h 2: NH3 / methanol / 6 h View Scheme

1: hydrogenchloride / 22 h / 25 °C 2: 1H-imidazole; triphenylphosphine; iodine / toluene / 2 h / 70 °C 3: zinc; water; hydrogenchloride / ethanol / 19 h / 10 - 24 °C 4: sodium carbonate; magnesium sulfate / ethanol; water / 23 h / 25 °C 5: toluene / 5 h / |Reflux 6: hydrogen; palladium 10 on activated carbon / methanol / 18 h / 30 °C / 2250.23 Torr View Scheme