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

With  triethylamine in  acetone 6 h;  Ambient temperature;   

With  sodium iodide; zinc in  N,N-dimethyl-formamide T=135°C; 3 h;   

Multi-step reaction with 3 steps 1: 70 percent / NaI, Zn / dimethylformamide / 3 h / 135 °C2: 75 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O; 2-methyl-propan-2-ol3: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) toluene, reflux 2.) toluene, 100 deg C, 8 h  

Multi-step reaction with 4 steps 1: 70 percent / NaI, Zn / dimethylformamide / 3 h / 135 °C2: 75 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O; 2-methyl-propan-2-ol3: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) toluene, reflux 2.) toluene, 100 deg C, 8 h4: 95 percent / pyridine / CH2Cl2 / 1 h  

Multi-step reaction with 5 steps 1: 70 percent / NaI, Zn / dimethylformamide / 3 h / 135 °C2: 75 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O; 2-methyl-propan-2-ol3: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) toluene, reflux 2.) toluene, 100 deg C, 8 h4: 95 percent / pyridine / CH2Cl2 / 1 h5: 10.6 g / lithium azide / CH2Cl2; dimethylformamide / 8 h / -40 °C  

Multi-step reaction with 6 steps 1: 70 percent / NaI, Zn / dimethylformamide / 3 h / 135 °C2: 75 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O; 2-methyl-propan-2-ol3: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) toluene, reflux 2.) toluene, 100 deg C, 8 h4: 95 percent / pyridine / CH2Cl2 / 1 h5: 10.6 g / lithium azide / CH2Cl2; dimethylformamide / 8 h / -40 °C6: NiCl2, NaBH4 / ethanol / 0 °C  

Multi-step reaction with 7 steps 1: 70 percent / NaI, Zn / dimethylformamide / 3 h / 135 °C2: 75 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O; 2-methyl-propan-2-ol3: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) toluene, reflux 2.) toluene, 100 deg C, 8 h4: 95 percent / pyridine / CH2Cl2 / 1 h5: 10.6 g / lithium azide / CH2Cl2; dimethylformamide / 8 h / -40 °C6: NiCl2, NaBH4 / ethanol / 0 °C7: 9.6 g / pyridine / 2 h / 40 °C  

Multi-step reaction with 8 steps 1: 70 percent / NaI, Zn / dimethylformamide / 3 h / 135 °C2: 75 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O; 2-methyl-propan-2-ol3: 1.) dibutyltin oxide, 2.) tetrabutylammonium bromide / 1.) toluene, reflux 2.) toluene, 100 deg C, 8 h4: 95 percent / pyridine / CH2Cl2 / 1 h5: 10.6 g / lithium azide / CH2Cl2; dimethylformamide / 8 h / -40 °C6: NiCl2, NaBH4 / ethanol / 0 °C7: 9.6 g / pyridine / 2 h / 40 °C8: 1.1 g / H2, glacial acetic acid / 10percent palladium-on-charcoal / methanol / 24 h / 2250.2 Torr  

Multi-step reaction with 2 steps 1: 70 percent / NaI, Zn / dimethylformamide / 3 h / 135 °C2: 75 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O; 2-methyl-propan-2-ol