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

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

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

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

hydrogen; palladium in acetic acid

3: NaN3 / dimethylformamide / 48 h / 70 °C 4: 1.) H2 / 1.) palladium black, ethanol; 2.) pyridine 5: 2.) sodium borohydride 6: H2 / palladium black / acetic acid View Scheme

2: NaN3 / dimethylformamide / 48 h / 70 °C 3: 1.) H2 / 1.) palladium black, ethanol; 2.) pyridine 4: 2.) sodium borohydride 5: H2 / palladium black / acetic acid View Scheme

1: pyridine / CH2Cl2 / -30 °C 2: NaN3 / dimethylformamide / 12 h / 60 °C 3: 1.) sodium hydrogen telluride / 2.) pyridine 4: 81 percent / aq. trifluoroacetic acid, sodium borohydride 5: 92 percent / H2 / palladium black / acetic acid View Scheme

1: NaN3 / dimethylformamide / 48 h / 70 °C 2: 1.) H2 / 1.) palladium black, ethanol; 2.) pyridine 3: 2.) sodium borohydride 4: H2 / palladium black / acetic acid View Scheme

1: NaN3 / dimethylformamide / 12 h / 60 °C 2: 1.) sodium hydrogen telluride / 2.) pyridine 3: 81 percent / aq. trifluoroacetic acid, sodium borohydride 4: 92 percent / H2 / palladium black / acetic acid View Scheme