1.1: 91 percent / NEt3 / CH2Cl2 2.1: OsO4; NMO / acetone; H2O / 120 °C 3.1: TsOH 4.1: 73 percent / 120 °C 5.1: TFA / CH2Cl2 5.2: NaIO4 / ethanol; H2O 5.3: NaBH4 / ethanol; H2O 6.1: 67 percent / HCOONH4 / Pd/C / methanol / Heating View Scheme

1.1: 80 percent / m-CPBA / toluene / 24 h / 20 °C 2.1: 63 percent / H2SO4; H2O / dioxane / 2.5 h / Heating 3.1: 100 percent / DMAP / pyridine; CH2Cl2 / 2 h 4.1: 67 percent / NaIO4 / RuCl3 / ethyl acetate; acetonitrile; H2O / 3 h / 20 °C 5.1: 100 percent / methanol / 0.25 h 6.1: LiBH4 / tetrahydrofuran / 8 h / 20 °C 6.2: DMAP; Ac2O / pyridine; CH2Cl2 / 2 h 6.3: aq. HCl / 18 h / Heating View Scheme

1.1: 95 percent / NaOAc / Pd2(dba)3*dba / acetonitrile / 0.33 h 2.1: HCO2H / ethyl acetate / 0.67 h 3.1: 80 percent / m-CPBA / toluene / 24 h / 20 °C 4.1: 63 percent / H2SO4; H2O / dioxane / 2.5 h / Heating 5.1: 100 percent / DMAP / pyridine; CH2Cl2 / 2 h 6.1: 67 percent / NaIO4 / RuCl3 / ethyl acetate; acetonitrile; H2O / 3 h / 20 °C 7.1: 100 percent / methanol / 0.25 h 8.1: LiBH4 / tetrahydrofuran / 8 h / 20 °C 8.2: DMAP; Ac2O / pyridine; CH2Cl2 / 2 h 8.3: aq. HCl / 18 h / Heating View Scheme

1.1: 100 percent / DMAP / pyridine; CH2Cl2 / 2 h 2.1: 67 percent / NaIO4 / RuCl3 / ethyl acetate; acetonitrile; H2O / 3 h / 20 °C 3.1: 100 percent / methanol / 0.25 h 4.1: LiBH4 / tetrahydrofuran / 8 h / 20 °C 4.2: DMAP; Ac2O / pyridine; CH2Cl2 / 2 h 4.3: aq. HCl / 18 h / Heating View Scheme

1.1: 67 percent / NaIO4 / RuCl3 / ethyl acetate; acetonitrile; H2O / 3 h / 20 °C 2.1: 100 percent / methanol / 0.25 h 3.1: LiBH4 / tetrahydrofuran / 8 h / 20 °C 3.2: DMAP; Ac2O / pyridine; CH2Cl2 / 2 h 3.3: aq. HCl / 18 h / Heating View Scheme

1: sodium methoxide / 3 h / Heating 2: acid resin (Dowex 50W-XH) / methanol / 12 h / Heating 3: pyridine / CH2Cl2; pyridine / 0.25 h / -30 °C 4: sodium azide / dimethylformamide / 24 h / 50 °C 5: 80 percent / sodium metoxide / methanol / 6 h / Ambient temperature 6: 81 percent / pyridine / 4 h / from 0 deg C to room temp. 7: 94 percent / pyridine / 4 h / Ambient temperature 8: 82 percent / sodium methoxide / dimethylformamide / 0.08 h / 50 °C 9: sodium methoxide / dimethylformamide / 3 h / 50 °C 10: hydrogen / palladium black / ethanol / 1 h 11: aq. sodium bicarbonate / diethyl ether / 2 h / Ambient temperature 12: 1.) 50percent aq. trifluoroacetic acid, 2.) sodium borohydride / 1.) room temp., 15 ethanol, min; 2.) water, room temp., 10 min 13: 70 percent / hydrogen / palladium black / acetic acid / 13 h View Scheme

1: hydrochloric acid / methanol; H2O / 20 h / Ambient temperature 2: sodium methoxide / 3 h / Heating 3: acid resin (Dowex 50W-XH) / methanol / 12 h / Heating 4: pyridine / CH2Cl2; pyridine / 0.25 h / -30 °C 5: sodium azide / dimethylformamide / 24 h / 50 °C 6: 80 percent / sodium metoxide / methanol / 6 h / Ambient temperature 7: 81 percent / pyridine / 4 h / from 0 deg C to room temp. 8: 94 percent / pyridine / 4 h / Ambient temperature 9: 82 percent / sodium methoxide / dimethylformamide / 0.08 h / 50 °C 10: sodium methoxide / dimethylformamide / 3 h / 50 °C 11: hydrogen / palladium black / ethanol / 1 h 12: aq. sodium bicarbonate / diethyl ether / 2 h / Ambient temperature 13: 1.) 50percent aq. trifluoroacetic acid, 2.) sodium borohydride / 1.) room temp., 15 ethanol, min; 2.) water, room temp., 10 min 14: 70 percent / hydrogen / palladium black / acetic acid / 13 h View Scheme

1: 94 percent / pyridine / 4 h / Ambient temperature 2: 82 percent / sodium methoxide / dimethylformamide / 0.08 h / 50 °C 3: sodium methoxide / dimethylformamide / 3 h / 50 °C 4: hydrogen / palladium black / ethanol / 1 h 5: aq. sodium bicarbonate / diethyl ether / 2 h / Ambient temperature 6: 1.) 50percent aq. trifluoroacetic acid, 2.) sodium borohydride / 1.) room temp., 15 ethanol, min; 2.) water, room temp., 10 min 7: 70 percent / hydrogen / palladium black / acetic acid / 13 h View Scheme

1: sodium azide / dimethylformamide / 24 h / 50 °C 2: 80 percent / sodium metoxide / methanol / 6 h / Ambient temperature 3: 81 percent / pyridine / 4 h / from 0 deg C to room temp. 4: 94 percent / pyridine / 4 h / Ambient temperature 5: 82 percent / sodium methoxide / dimethylformamide / 0.08 h / 50 °C 6: sodium methoxide / dimethylformamide / 3 h / 50 °C 7: hydrogen / palladium black / ethanol / 1 h 8: aq. sodium bicarbonate / diethyl ether / 2 h / Ambient temperature 9: 1.) 50percent aq. trifluoroacetic acid, 2.) sodium borohydride / 1.) room temp., 15 ethanol, min; 2.) water, room temp., 10 min 10: 70 percent / hydrogen / palladium black / acetic acid / 13 h View Scheme

1: 82 percent / sodium methoxide / dimethylformamide / 0.08 h / 50 °C 2: sodium methoxide / dimethylformamide / 3 h / 50 °C 3: hydrogen / palladium black / ethanol / 1 h 4: aq. sodium bicarbonate / diethyl ether / 2 h / Ambient temperature 5: 1.) 50percent aq. trifluoroacetic acid, 2.) sodium borohydride / 1.) room temp., 15 ethanol, min; 2.) water, room temp., 10 min 6: 70 percent / hydrogen / palladium black / acetic acid / 13 h View Scheme