1: With lithium triethylborohydride in tetrahydrofuran 0.5 h; Cooling with iceInert atmosphere; 2: With hydrogenchloride in water T=20°C; pH=3; 48 h; Inert atmosphere;

1: With lithium triethylborohydride in tetrahydrofuran 0.5 h; Cooling with iceInert atmosphere; 2: With hydrogenchloride in water T=20°C; pH=3; 48 h; Inert atmosphere;

1: 84 percent / NaH / tetrahydrofuran; various solvent(s) / 1 h / Heating 2: 81 percent / aq. TFA / CH2Cl2 / 0 °C 3: 75 percent / Et3N / CH2Cl2 / 1.5 h / 0 °C 4: Et3N / CH2Cl2 / 0.5 h / 0 °C 5: 0.314 g / lithium aluminum hydride / tetrahydrofuran / 4 h / Heating 6: 64 percent / O3; aq. NaOH / CH2Cl2; methanol / -78 - 20 °C 7: 90 percent / H2 / Pd/C / ethanol View Scheme

1: 81 percent / aq. TFA / CH2Cl2 / 0 °C 2: 75 percent / Et3N / CH2Cl2 / 1.5 h / 0 °C 3: Et3N / CH2Cl2 / 0.5 h / 0 °C 4: 0.314 g / lithium aluminum hydride / tetrahydrofuran / 4 h / Heating 5: 64 percent / O3; aq. NaOH / CH2Cl2; methanol / -78 - 20 °C 6: 90 percent / H2 / Pd/C / ethanol View Scheme

1: 75 percent / Et3N / CH2Cl2 / 1.5 h / 0 °C 2: Et3N / CH2Cl2 / 0.5 h / 0 °C 3: 0.314 g / lithium aluminum hydride / tetrahydrofuran / 4 h / Heating 4: 64 percent / O3; aq. NaOH / CH2Cl2; methanol / -78 - 20 °C 5: 90 percent / H2 / Pd/C / ethanol View Scheme

1: Et3N / CH2Cl2 / 0.5 h / 0 °C 2: 0.314 g / lithium aluminum hydride / tetrahydrofuran / 4 h / Heating 3: 64 percent / O3; aq. NaOH / CH2Cl2; methanol / -78 - 20 °C 4: 90 percent / H2 / Pd/C / ethanol View Scheme

1: 0.314 g / lithium aluminum hydride / tetrahydrofuran / 4 h / Heating 2: 64 percent / O3; aq. NaOH / CH2Cl2; methanol / -78 - 20 °C 3: 90 percent / H2 / Pd/C / ethanol View Scheme

1: 64 percent / O3; aq. NaOH / CH2Cl2; methanol / -78 - 20 °C 2: 90 percent / H2 / Pd/C / ethanol View Scheme

1: 1) t-butyl hydroperoxide, 2) 10 percent Na2SO3 / 2) CH2Cl2, 3 h 2: 95 percent / p-TsOH / 1 h / Ambient temperature 3: 92 percent / LiAlH4 / diethyl ether / 16 h / Ambient temperature 4: 1) potassium hydride / 1) THF, 0 deg C, 30 min, 2) THF, RT, 16 h 6: tri-n-butylphosphine / CH2Cl2 / 0 deg C, 4 h then RT, 6 h 7: 4 M aq. HCl / CH2Cl2 / 1 h / 0 °C 8: 100 percent / N-(p-toluenesulfonyl)phenyloxaziridine, diisopropylamine / CHCl3 / 1) 0 deg C, 1.5 h, 2) RT, 20 h, 3) reflux, 1 h 9: 67 percent / pyridinium dichromate / dimethylformamide / 36 h / Ambient temperature 10: 1) ozone, 2) NaBH4 / 1) MeOH, CH2Cl2, -78 deg C, 5 min, 2) 20 h, 0 deg C 11: 88 percent / ammonium formate / 10 percent Pd/C / methanol / 2 h / Heating View Scheme

1: 95 percent / p-TsOH / 1 h / Ambient temperature 2: 92 percent / LiAlH4 / diethyl ether / 16 h / Ambient temperature 3: 1) potassium hydride / 1) THF, 0 deg C, 30 min, 2) THF, RT, 16 h 5: tri-n-butylphosphine / CH2Cl2 / 0 deg C, 4 h then RT, 6 h 6: 4 M aq. HCl / CH2Cl2 / 1 h / 0 °C 7: 100 percent / N-(p-toluenesulfonyl)phenyloxaziridine, diisopropylamine / CHCl3 / 1) 0 deg C, 1.5 h, 2) RT, 20 h, 3) reflux, 1 h 8: 67 percent / pyridinium dichromate / dimethylformamide / 36 h / Ambient temperature 9: 1) ozone, 2) NaBH4 / 1) MeOH, CH2Cl2, -78 deg C, 5 min, 2) 20 h, 0 deg C 10: 88 percent / ammonium formate / 10 percent Pd/C / methanol / 2 h / Heating View Scheme