1: 94 percent / H2 / Raney nickel / ethanol / 2 h 2: 54 percent / 15M KOH / aq. ethanol / 144 h / 90 °C 3: 74 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / Heating 4: 72 percent / cyclohexene / 20percent Pd(OH)2/C / ethanol / 44 h / Heating View Scheme

1: 62 percent / sodium azide / H2O; dimethylformamide 2: 56 percent / camphorsulphonic acid / methanol; H2O 3: 95 percent / barium methoxide / methanol 5: tetrahydrofuran 6: 80 percent / hydrogen / palladium on carbon / ethanol 7: 92 percent / sodium methoxide / methanol 8: 1.) borane, dimethyl sulphide; 2.) aq. trifluoroacetic acid View Scheme

2: tetrahydrofuran 3: 80 percent / hydrogen / palladium on carbon / ethanol 4: 92 percent / sodium methoxide / methanol 5: 1.) borane, dimethyl sulphide; 2.) aq. trifluoroacetic acid View Scheme

1: 95 percent / barium methoxide / methanol 3: tetrahydrofuran 4: 80 percent / hydrogen / palladium on carbon / ethanol 5: 92 percent / sodium methoxide / methanol 6: 1.) borane, dimethyl sulphide; 2.) aq. trifluoroacetic acid View Scheme

1: 80 percent / hydrogen / palladium on carbon / ethanol 2: 92 percent / sodium methoxide / methanol 3: 1.) borane, dimethyl sulphide; 2.) aq. trifluoroacetic acid View Scheme

1: 56 percent / camphorsulphonic acid / methanol; H2O 2: 95 percent / barium methoxide / methanol 4: tetrahydrofuran 5: 80 percent / hydrogen / palladium on carbon / ethanol 6: 92 percent / sodium methoxide / methanol 7: 1.) borane, dimethyl sulphide; 2.) aq. trifluoroacetic acid View Scheme

1: 83 percent / acetyl chloride / 50 deg C for 1.5 h then room temperature for 24 h 2: 89 percent / imidazole / dimethylformamide / 6 h / Ambient temperature 3: 97 percent / camphorsulphonic acid / acetone / 16 h / Ambient temperature 4: pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 2 h / Ambient temperature; molecular sieve 3 A 5: sodium borohydride / ethanol / 1 h / 0 °C 6: pyridine / CH2Cl2 / 8 h / -20 °C 7: sodium azide / dimethylformamide / 16 h / Ambient temperature 8: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature 9: 100 percent / hydrogen / palladium black / methanol / 1 h / Ambient temperature 10: aq. sodium bicarbonate / diethyl ether / 1.5 h / 0 °C 11: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 1.5 h / Ambient temperature 12: 59 percent / CH2Cl2 / 16 h / Ambient temperature 13: 61 percent / hydrogen / palladium black / methanol / 48 h 14: H2 / palladium black / acetic acid / 72 h / Ambient temperature 15: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme

1: aq. sodium bicarbonate / diethyl ether / 1.5 h / 0 °C 2: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 1.5 h / Ambient temperature 3: 59 percent / CH2Cl2 / 16 h / Ambient temperature 4: 61 percent / hydrogen / palladium black / methanol / 48 h 5: H2 / palladium black / acetic acid / 72 h / Ambient temperature 6: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme

1: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 1.5 h / Ambient temperature 2: 59 percent / CH2Cl2 / 16 h / Ambient temperature 3: 61 percent / hydrogen / palladium black / methanol / 48 h 4: H2 / palladium black / acetic acid / 72 h / Ambient temperature 5: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme

1: 59 percent / CH2Cl2 / 16 h / Ambient temperature 2: 61 percent / hydrogen / palladium black / methanol / 48 h 3: H2 / palladium black / acetic acid / 72 h / Ambient temperature 4: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme