hydrogen; palladium on activated charcoal in methanol T=20°C; 13 h;

hydrogen; trifluoroacetic acid; platinum(IV) oxide in ethanol; water 15 h; Ambient temperature;

[14C]-2-Ketoglutaric acid; iron(II) sulfate; ascorbic acid powder; Aeromonas caviae in water T=25°C; pH=7; 24 h; Enzymatic reaction;

hydrogenchloride in ethanol 3 h; Inert atmosphereReflux;

1.1: 98 percent / imidazole / dimethylformamide / 12 h / 20 °C 2.1: BH3*SMe2 / tetrahydrofuran / 10 h / 20 °C 2.2: 70 percent / NaOH; aq. H2O2 / tetrahydrofuran 3.1: 87 percent / MsCl; Et3N / tetrahydrofuran / 3 h / 0 °C 4.1: H2 / Pd/C / methanol / 3 h / 60 °C 5.1: 0.14 g / Dowex 50W-X8; H2O / tetrahydrofuran / Heating View Scheme

1: 63 percent / t-BuOOH, n-Bu4NF, K2CO3 / dimethylformamide; 2,2,4-trimethyl-pentane; tetrahydrofuran / 2 h 2: 79 percent / aluminum amalgam, NaHCO3 (half sat.) / ethanol; acetone / 2 h 3: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C 4: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h 5: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr 6: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 7: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme

1: 1.) n-BuLi, hexamethyldisilazane / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h 2: 30percent aq. H2O2 / ethyl acetate / 0.67 h / 0 - 22 °C 3: 63 percent / t-BuOOH, n-Bu4NF, K2CO3 / dimethylformamide; 2,2,4-trimethyl-pentane; tetrahydrofuran / 2 h 4: 79 percent / aluminum amalgam, NaHCO3 (half sat.) / ethanol; acetone / 2 h 5: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C 6: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h 7: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr 8: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 9: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme

1: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C 2: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h 3: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr 4: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 5: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme

1: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr 2: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 3: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme

1: 1.) BH3*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et2O, RT, 6 h 2: 80 percent / H2 / 10percent Pd/C / methanol / 3 h / 15001.2 Torr 3: 51 percent / NaIO4, RuCl3 / acetonitrile; CCl4; H2O / 1.5 h / Ambient temperature 4: 70 percent / 6 M aq. HCl / 3 h / Heating View Scheme