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

Multi-step reaction with 2 steps 1: 1.) LiAlH4; 2.) pyridine; 3.) NaN3 / 1.) THF; 3.) DMF, 130 deg C2: 65 percent / H2 / Pd black / ethanol  

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  

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 10 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: N,N-diethylaniline6: 10 percent HCl / methanol / 40 °C7: NaH / tetrahydrofuran; dimethylformamide8: 10 percent HCl / methanol / 70 °C9: 2.) copper(I) iodide / 2.) THF, dimethylsulfide10: NaH / tetrahydrofuran; dimethylformamide  

Multi-step reaction with 9 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: N,N-diethylaniline6: 10 percent HCl / methanol / 40 °C7: NaH / tetrahydrofuran; dimethylformamide8: 10 percent HCl / methanol / 70 °C9: 2.) copper(I) iodide / 2.) THF, dimethylsulfide  

Multi-step reaction with 11 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: N,N-diethylaniline6: 10 percent HCl / methanol / 40 °C7: NaH / tetrahydrofuran; dimethylformamide8: 10 percent HCl / methanol / 70 °C9: 2.) copper(I) iodide / 2.) THF, dimethylsulfide10: NaH / tetrahydrofuran; dimethylformamide11: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF  

Multi-step reaction with 12 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: N,N-diethylaniline6: 10 percent HCl / methanol / 40 °C7: NaH / tetrahydrofuran; dimethylformamide8: 10 percent HCl / methanol / 70 °C9: 2.) copper(I) iodide / 2.) THF, dimethylsulfide10: NaH / tetrahydrofuran; dimethylformamide11: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF12: mesyl chloride, triethylamine / CH2Cl2