potassium permanganate in acetone 48 h;

hydrogen; palladium on activated charcoal in acetic acid P=760 Torr; Ambient temperature;

sodium hydroxide in ethanol Ambient temperature;

1: 61 percent / CH3COONH4 / acetic acid / 1.5 h / Heating 2: LiAlH4 / tetrahydrofuran; diethyl ether / 0.83 h / Heating 3: 76 percent / 10percent NaOH / CH2Cl2 / 0.5 h / Ambient temperature 4: 98 percent / 4-dimethylaminopyridine / acetonitrile / 67 h / Ambient temperature 5: 1.) OsO4, pyridine, 2.) sodium hydrogen sulfite / 1.) RT, 3.5 h, 2.) water, RT, 2.5 h 6: 76 percent / NaIO4 / methanol; H2O / 0.08 h / Ambient temperature 7: 100 percent / K2CO3 / dimethylformamide / 2 h / 40 °C 8: 86 percent / TFA / CH2Cl2 / 0.17 h / Ambient temperature 9: H2 / 10percent Pd/C / acetic acid / 760 Torr / Ambient temperature View Scheme

1: LiAlH4 / tetrahydrofuran; diethyl ether / 0.83 h / Heating 2: 76 percent / 10percent NaOH / CH2Cl2 / 0.5 h / Ambient temperature 3: 98 percent / 4-dimethylaminopyridine / acetonitrile / 67 h / Ambient temperature 4: 1.) OsO4, pyridine, 2.) sodium hydrogen sulfite / 1.) RT, 3.5 h, 2.) water, RT, 2.5 h 5: 76 percent / NaIO4 / methanol; H2O / 0.08 h / Ambient temperature 6: 100 percent / K2CO3 / dimethylformamide / 2 h / 40 °C 7: 86 percent / TFA / CH2Cl2 / 0.17 h / Ambient temperature 8: H2 / 10percent Pd/C / acetic acid / 760 Torr / Ambient temperature View Scheme

1: 98 percent / 4-dimethylaminopyridine / acetonitrile / 67 h / Ambient temperature 2: 1.) OsO4, pyridine, 2.) sodium hydrogen sulfite / 1.) RT, 3.5 h, 2.) water, RT, 2.5 h 3: 76 percent / NaIO4 / methanol; H2O / 0.08 h / Ambient temperature 4: 100 percent / K2CO3 / dimethylformamide / 2 h / 40 °C 5: 86 percent / TFA / CH2Cl2 / 0.17 h / Ambient temperature 6: H2 / 10percent Pd/C / acetic acid / 760 Torr / Ambient temperature View Scheme

1: 100 percent / K2CO3 / dimethylformamide / 2 h / 40 °C 2: 86 percent / TFA / CH2Cl2 / 0.17 h / Ambient temperature 3: H2 / 10percent Pd/C / acetic acid / 760 Torr / Ambient temperature View Scheme

1: 1.) OsO4, pyridine, 2.) sodium hydrogen sulfite / 1.) RT, 3.5 h, 2.) water, RT, 2.5 h 2: 76 percent / NaIO4 / methanol; H2O / 0.08 h / Ambient temperature 3: 100 percent / K2CO3 / dimethylformamide / 2 h / 40 °C 4: 86 percent / TFA / CH2Cl2 / 0.17 h / Ambient temperature 5: H2 / 10percent Pd/C / acetic acid / 760 Torr / Ambient temperature View Scheme

1: 86 percent / TFA / CH2Cl2 / 0.17 h / Ambient temperature 2: H2 / 10percent Pd/C / acetic acid / 760 Torr / Ambient temperature View Scheme

1: 76 percent / NaIO4 / methanol; H2O / 0.08 h / Ambient temperature 2: 100 percent / K2CO3 / dimethylformamide / 2 h / 40 °C 3: 86 percent / TFA / CH2Cl2 / 0.17 h / Ambient temperature 4: H2 / 10percent Pd/C / acetic acid / 760 Torr / Ambient temperature View Scheme