1: 67 percent / DBU; ozone / tetrahydrofuran / 3 h / -78 - 20 °C 2: 62 percent / PPh3; DEAD / tetrahydrofuran / 6 h / 0 °C 3: 79 percent / DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 4: 89 percent / OsO4; NMO / acetone; H2O / 12 h / 20 °C 5: 71 percent / pyridine / 10 h / 20 °C 6: 71 percent / TsOH*H2O / 6 h / 20 °C 7: 61 percent / FeCl3*6H2O/SiO2 / CH2Cl2 / 15 h / 20 °C 8: 95 percent / pyridine / 10 h / 20 °C 9: 60 percent / DMF; SOCl2 / pyridine / 8 h / 20 °C 10: 73 percent / NH3 / methanol / 192 h / 20 °C 11: 91 percent / 1 M aq. HCl / 6 h / 80 °C View Scheme

1: 79 percent / DIBAL-H / CH2Cl2; hexane / 1 h / -78 °C 2: 89 percent / OsO4; NMO / acetone; H2O / 12 h / 20 °C 3: 71 percent / pyridine / 10 h / 20 °C 4: 71 percent / TsOH*H2O / 6 h / 20 °C 5: 61 percent / FeCl3*6H2O/SiO2 / CH2Cl2 / 15 h / 20 °C 6: 95 percent / pyridine / 10 h / 20 °C 7: 60 percent / DMF; SOCl2 / pyridine / 8 h / 20 °C 8: 73 percent / NH3 / methanol / 192 h / 20 °C 9: 91 percent / 1 M aq. HCl / 6 h / 80 °C View Scheme

1: 89 percent / OsO4; NMO / acetone; H2O / 12 h / 20 °C 2: 71 percent / pyridine / 10 h / 20 °C 3: 71 percent / TsOH*H2O / 6 h / 20 °C 4: 61 percent / FeCl3*6H2O/SiO2 / CH2Cl2 / 15 h / 20 °C 5: 95 percent / pyridine / 10 h / 20 °C 6: 60 percent / DMF; SOCl2 / pyridine / 8 h / 20 °C 7: 73 percent / NH3 / methanol / 192 h / 20 °C 8: 91 percent / 1 M aq. HCl / 6 h / 80 °C View Scheme

1: NaBH4 / methanol / 3 h / Heating 2: NaIO4 / 0.5 h / Ambient temperature 3: 2.42 g 4: 73 percent / p-(dimethylamino)pyridine, triethylamine / tetrahydrofuran / 16 h / Ambient temperature 5: 44.7 percent / silver trifluoroacetate / CH2Cl2 / 2 h / Ambient temperature 6: 87 percent / diisopropylethylamine / CH2Cl2 / 16 h / Ambient temperature 7: 108 mg / 0.13M NaOH / acetone / 2 h 8: 1.) triethylamine, ethyl chloroformate, 2.) sodium azide 9: 98.6 percent / O3 / CH2Cl2 / 0.25 h / -78 °C 10: 101 mg / 2.5N NaOH / methanol / 12 h / Heating 11: 116 mg / triethylamine / butan-1-ol / 40 h / Heating 12: 1.) acetic anhydride, 2.) NH3(gas) / 1.) room temperature, 2 h, 2.) methanol, 45 deg C, 16 h 13: 80 percent / 2M HCl / methanol / 16 h / Ambient temperature View Scheme

1: 1.) pig liver esterase, 2.) O3 / 1.) acetone, 30-32 deg C, 5 h, 2.) ethyl acetate, -78 deg C, 3 h 2: NaBH4 / methanol / 3 h / Heating 3: NaIO4 / 0.5 h / Ambient temperature 4: 2.42 g 5: 73 percent / p-(dimethylamino)pyridine, triethylamine / tetrahydrofuran / 16 h / Ambient temperature 6: 44.7 percent / silver trifluoroacetate / CH2Cl2 / 2 h / Ambient temperature 7: 87 percent / diisopropylethylamine / CH2Cl2 / 16 h / Ambient temperature 8: 108 mg / 0.13M NaOH / acetone / 2 h 9: 1.) triethylamine, ethyl chloroformate, 2.) sodium azide 10: 98.6 percent / O3 / CH2Cl2 / 0.25 h / -78 °C 11: 101 mg / 2.5N NaOH / methanol / 12 h / Heating 12: 116 mg / triethylamine / butan-1-ol / 40 h / Heating 13: 1.) acetic anhydride, 2.) NH3(gas) / 1.) room temperature, 2 h, 2.) methanol, 45 deg C, 16 h 14: 80 percent / 2M HCl / methanol / 16 h / Ambient temperature View Scheme

1: 97 percent / NaBH4, CeCl3*7H2O / methanol / 0.17 h / 0 - 5 °C 2: 100 percent / Et3N / CH2Cl2 / 0.17 h / -5 - 0 °C 3: 74 percent / LiN3, P(NMe2)3 / dimethylsulfoxide / Ambient temperature 4: H2 / Lindlar's catalyst / butan-1-ol / 3 h / 760 Torr 5: Et3N / butan-1-ol / 20 h / Heating 6: conc. HCl / 42 h / Ambient temperature 7: 70 percent / liquid NH3 / methanol / 18 h / 60 °C 8: 50 percent / 1 M BCl3 / CH2Cl2; hexane / 2.5 h / -75 °C View Scheme

1: 91 percent / m-chloroperbenzoic acid / CH2Cl2 / 16 h / Ambient temperature 2: 1.) trimethylsiolyl triflate, 2,6-lutidine, 2.) DBU, 3.) K2CO3 3: 99 mg / diisopropylethylamine / CH2Cl2 / 16 h / Ambient temperature 4: 101 mg / 2.5N NaOH / methanol / 12 h / Heating 5: 116 mg / triethylamine / butan-1-ol / 40 h / Heating 6: 1.) acetic anhydride, 2.) NH3(gas) / 1.) room temperature, 2 h, 2.) methanol, 45 deg C, 16 h 7: 80 percent / 2M HCl / methanol / 16 h / Ambient temperature View Scheme

1: 1.) triethylamine, ethyl chloroformate, 2.) NaN3 2: 95 percent / 1.) O3, 2.) pyridine / CH2Cl2 / 1.) -78 deg C, 15 min, 2.) reflux, 2 h 3: 91 percent / m-chloroperbenzoic acid / CH2Cl2 / 16 h / Ambient temperature 4: 1.) trimethylsiolyl triflate, 2,6-lutidine, 2.) DBU, 3.) K2CO3 5: 99 mg / diisopropylethylamine / CH2Cl2 / 16 h / Ambient temperature 6: 101 mg / 2.5N NaOH / methanol / 12 h / Heating 7: 116 mg / triethylamine / butan-1-ol / 40 h / Heating 8: 1.) acetic anhydride, 2.) NH3(gas) / 1.) room temperature, 2 h, 2.) methanol, 45 deg C, 16 h 9: 80 percent / 2M HCl / methanol / 16 h / Ambient temperature View Scheme

1: 95 percent / 1.) O3, 2.) pyridine / CH2Cl2 / 1.) -78 deg C, 15 min, 2.) reflux, 2 h 2: 91 percent / m-chloroperbenzoic acid / CH2Cl2 / 16 h / Ambient temperature 3: 1.) trimethylsiolyl triflate, 2,6-lutidine, 2.) DBU, 3.) K2CO3 4: 99 mg / diisopropylethylamine / CH2Cl2 / 16 h / Ambient temperature 5: 101 mg / 2.5N NaOH / methanol / 12 h / Heating 6: 116 mg / triethylamine / butan-1-ol / 40 h / Heating 7: 1.) acetic anhydride, 2.) NH3(gas) / 1.) room temperature, 2 h, 2.) methanol, 45 deg C, 16 h 8: 80 percent / 2M HCl / methanol / 16 h / Ambient temperature View Scheme

1: H2 / Lindlar's catalyst / butan-1-ol / 3 h / 760 Torr 2: Et3N / butan-1-ol / 20 h / Heating 3: conc. HCl / 42 h / Ambient temperature 4: 70 percent / liquid NH3 / methanol / 18 h / 60 °C 5: 50 percent / 1 M BCl3 / CH2Cl2; hexane / 2.5 h / -75 °C View Scheme