1: p-TsOH / acetone 2: 1.) LiAlH4; 2.) pyridine; 3.) NaN3 / 1.) THF; 3.) DMF, 130 deg C 3: 65 percent / H2 / Pd black / ethanol 4: K2CO3 / ethanol 5: cc. HCl / methanol 6: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide 7: NaH / tetrahydrofuran; dimethylformamide 8: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF 9: mesyl chloride, triethylamine / CH2Cl2 View Scheme

Multi-step reaction with 3 steps 1: p-TsOH / acetone2: 1.) LiAlH4; 2.) pyridine; 3.) NaN3 / 1.) THF; 3.) DMF, 130 deg C3: 65 percent / H2 / Pd black / ethanol  

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 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 11 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: N,N-diethylaniline7: 10 percent HCl / methanol / 40 °C8: NaH / tetrahydrofuran; dimethylformamide9: 10 percent HCl / methanol / 70 °C10: 2.) copper(I) iodide / 2.) THF, dimethylsulfide11: NaH / tetrahydrofuran; dimethylformamide  

Multi-step reaction with 10 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: N,N-diethylaniline7: 10 percent HCl / methanol / 40 °C8: NaH / tetrahydrofuran; dimethylformamide9: 10 percent HCl / methanol / 70 °C10: 2.) copper(I) iodide / 2.) THF, dimethylsulfide  

Multi-step reaction with 12 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: N,N-diethylaniline7: 10 percent HCl / methanol / 40 °C8: NaH / tetrahydrofuran; dimethylformamide9: 10 percent HCl / methanol / 70 °C10: 2.) copper(I) iodide / 2.) THF, dimethylsulfide11: NaH / tetrahydrofuran; dimethylformamide12: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF  

Multi-step reaction with 13 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: N,N-diethylaniline7: 10 percent HCl / methanol / 40 °C8: NaH / tetrahydrofuran; dimethylformamide9: 10 percent HCl / methanol / 70 °C10: 2.) copper(I) iodide / 2.) THF, dimethylsulfide11: NaH / tetrahydrofuran; dimethylformamide12: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF13: mesyl chloride, triethylamine / CH2Cl2