1: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide 2: NaH / tetrahydrofuran; dimethylformamide 3: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF 4: mesyl chloride, triethylamine / CH2Cl2 View Scheme

Multi-step reaction with 4 steps 1: OsO4 2: p-TsOH / acetone3: H2 / Pd black / methanol4: borane, dimethylsulfide / tetrahydrofuran  

Multi-step reaction with 5 steps 1: p-TsOH / acetone2: 1.) LiAlH4; 2.) pyridine; 3.) NaN3 / 1.) THF; 3.) DMF, 130 deg C3: 65 percent / H2 / Pd black / ethanol4: K2CO3 / ethanol5: cc. HCl / methanol  

Multi-step reaction with 4 steps 1: 1.) LiAlH4; 2.) pyridine; 3.) NaN3 / 1.) THF; 3.) DMF, 130 deg C2: 65 percent / H2 / Pd black / ethanol3: K2CO3 / ethanol4: cc. HCl / methanol