1: NaH / tetrahydrofuran; dimethylformamide 2: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF 3: mesyl chloride, triethylamine / CH2Cl2 View Scheme

Multi-step reaction with 5 steps 1: OsO4 2: p-TsOH / acetone3: H2 / Pd black / methanol4: borane, dimethylsulfide / tetrahydrofuran5: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide  

Multi-step reaction with 6 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 / methanol6: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide  

Multi-step reaction with 5 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 / methanol5: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide  

Multi-step reaction with 4 steps 1: p-TsOH / acetone2: H2 / Pd black / methanol3: borane, dimethylsulfide / tetrahydrofuran4: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide