1: aq. H2SO4 / 3.25 h / 60 °C 2: sodium cyanoborohydride / methanol / 336 h / in a refrigerator 3: 49 percent / H2, HCl / Pd(OH)2 on carbon / methanol / 5 h / 760 Torr View Scheme

1: 1) PPh3, 2) H2O / 1) THF, ambient temperature, 10 h, 2) THF, 10 h 2: pyridine / 0.5 h 3: 70 percent / H2 / Pd(OH)2/C / ethanol View Scheme

1: pyridine / CH2Cl2 / 0.25 h 2: NaN3 / dimethylformamide / 1 h / Ambient temperature 3: 1) PPh3, 2) H2O / 1) THF, ambient temperature, 10 h, 2) THF, 10 h 4: pyridine / 0.5 h 5: 70 percent / H2 / Pd(OH)2/C / ethanol View Scheme

1: potassium carbonate / dimethylformamide / 2 h 2: 249.3 g / p-toluenesulfonic acid / dimethylformamide; various solvent(s) / 2 h / 30 °C 3: 97 percent / triethylamine / acetone / 6 h / Ambient temperature 4: 70 percent / NaI, Zn / dimethylformamide / 3 h / 135 °C 5: 75 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O; 2-methyl-propan-2-ol 6: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) toluene, reflux 2.) toluene, 100 deg C, 8 h 7: 95 percent / pyridine / CH2Cl2 / 1 h 8: 10.6 g / lithium azide / CH2Cl2; dimethylformamide / 8 h / -40 °C 9: NiCl2, NaBH4 / ethanol / 0 °C 10: 9.6 g / pyridine / 2 h / 40 °C 11: 1.1 g / H2, glacial acetic acid / 10percent palladium-on-charcoal / methanol / 24 h / 2250.2 Torr 12: 100 percent / glacial acetic acid / H2O / 8 h / 60 °C View Scheme

1: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) toluene, reflux 2.) toluene, 100 deg C, 8 h 2: 95 percent / pyridine / CH2Cl2 / 1 h 3: 10.6 g / lithium azide / CH2Cl2; dimethylformamide / 8 h / -40 °C 4: NiCl2, NaBH4 / ethanol / 0 °C 5: 9.6 g / pyridine / 2 h / 40 °C 6: 1.1 g / H2, glacial acetic acid / 10percent palladium-on-charcoal / methanol / 24 h / 2250.2 Torr 7: 100 percent / glacial acetic acid / H2O / 8 h / 60 °C View Scheme

1: 249.3 g / p-toluenesulfonic acid / dimethylformamide; various solvent(s) / 2 h / 30 °C 2: 97 percent / triethylamine / acetone / 6 h / Ambient temperature 3: 70 percent / NaI, Zn / dimethylformamide / 3 h / 135 °C 4: 75 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O; 2-methyl-propan-2-ol 5: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) toluene, reflux 2.) toluene, 100 deg C, 8 h 6: 95 percent / pyridine / CH2Cl2 / 1 h 7: 10.6 g / lithium azide / CH2Cl2; dimethylformamide / 8 h / -40 °C 8: NiCl2, NaBH4 / ethanol / 0 °C 9: 9.6 g / pyridine / 2 h / 40 °C 10: 1.1 g / H2, glacial acetic acid / 10percent palladium-on-charcoal / methanol / 24 h / 2250.2 Torr 11: 100 percent / glacial acetic acid / H2O / 8 h / 60 °C View Scheme

1: 75 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O; 2-methyl-propan-2-ol 2: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) toluene, reflux 2.) toluene, 100 deg C, 8 h 3: 95 percent / pyridine / CH2Cl2 / 1 h 4: 10.6 g / lithium azide / CH2Cl2; dimethylformamide / 8 h / -40 °C 5: NiCl2, NaBH4 / ethanol / 0 °C 6: 9.6 g / pyridine / 2 h / 40 °C 7: 1.1 g / H2, glacial acetic acid / 10percent palladium-on-charcoal / methanol / 24 h / 2250.2 Torr 8: 100 percent / glacial acetic acid / H2O / 8 h / 60 °C View Scheme

1: 95 percent / pyridine / CH2Cl2 / 1 h 2: 10.6 g / lithium azide / CH2Cl2; dimethylformamide / 8 h / -40 °C 3: NiCl2, NaBH4 / ethanol / 0 °C 4: 9.6 g / pyridine / 2 h / 40 °C 5: 1.1 g / H2, glacial acetic acid / 10percent palladium-on-charcoal / methanol / 24 h / 2250.2 Torr 6: 100 percent / glacial acetic acid / H2O / 8 h / 60 °C View Scheme

1: 9.6 g / pyridine / 2 h / 40 °C 2: 1.1 g / H2, glacial acetic acid / 10percent palladium-on-charcoal / methanol / 24 h / 2250.2 Torr 3: 100 percent / glacial acetic acid / H2O / 8 h / 60 °C View Scheme

1: 1.1 g / H2, glacial acetic acid / 10percent palladium-on-charcoal / methanol / 24 h / 2250.2 Torr 2: 100 percent / glacial acetic acid / H2O / 8 h / 60 °C View Scheme