1: borane, dimethylsulfide / tetrahydrofuran 2: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide 3: NaH / tetrahydrofuran; dimethylformamide 4: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF 5: mesyl chloride, triethylamine / CH2Cl2 View Scheme

1: OsO4 2: p-TsOH / acetone 3: H2 / Pd black / methanol 4: borane, dimethylsulfide / tetrahydrofuran 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

1: 52 percent / OsO4, N-methylmorpholine N-oxide / H2O; acetone 2: p-TsOH / acetone 3: 1.) LiAlH4; 2.) pyridine; 3.) NaN3 / 1.) THF; 3.) DMF, 130 deg C 4: 65 percent / H2 / Pd black / ethanol 5: K2CO3 / ethanol 6: cc. HCl / methanol 7: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide 8: NaH / tetrahydrofuran; dimethylformamide 9: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF 10: mesyl chloride, triethylamine / CH2Cl2 View Scheme

1: H2 / Pd black / methanol 2: borane, dimethylsulfide / tetrahydrofuran 3: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide 4: NaH / tetrahydrofuran; dimethylformamide 5: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF 6: mesyl chloride, triethylamine / CH2Cl2 View Scheme

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

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

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

1: cc. HCl / methanol 2: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide 3: NaH / tetrahydrofuran; dimethylformamide 4: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF 5: mesyl chloride, triethylamine / CH2Cl2 View Scheme

1: p-TsOH / acetone 2: H2 / Pd black / methanol 3: borane, dimethylsulfide / tetrahydrofuran 4: 1.) copper(I) iodide / 1.) Swern oxidation; 2.) THF, -78 deg C, dimethylsulfide 5: NaH / tetrahydrofuran; dimethylformamide 6: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF 7: mesyl chloride, triethylamine / CH2Cl2 View Scheme

1: 89 percent / imidazole / dimethylformamide / 6 h / Ambient temperature 2: 97 percent / camphorsulphonic acid / acetone / 16 h / Ambient temperature 3: pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 2 h / Ambient temperature; molecular sieve 3 A 4: sodium borohydride / ethanol / 1 h / 0 °C 5: pyridine / CH2Cl2 / 8 h / -20 °C 6: sodium azide / dimethylformamide / 16 h / Ambient temperature 7: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature 8: 100 percent / hydrogen / palladium black / methanol / 1 h / Ambient temperature 9: aq. sodium bicarbonate / diethyl ether / 1.5 h / 0 °C 10: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 1.5 h / Ambient temperature 11: 59 percent / CH2Cl2 / 16 h / Ambient temperature 12: 61 percent / hydrogen / palladium black / methanol / 48 h 13: H2 / palladium black / acetic acid / 72 h / Ambient temperature 14: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme