1: With sodium tetrahydroborate; dmgH2; cobalt(II) chloride; sodium hydroxide in tetrahydrofuran; water T=15 - 20°C; 0.5 h; 2: With acetic acid in tetrahydrofuran; water T=15 - 20°C; pH=Ca. 10; ConcentrationpH-value;

1: 63 percent / NaH / dimethylformamide 2: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 3: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 4: 70percent m-chloroperbenzoic acid / methanol / Heating 5: 80 °C 6: NaOAc / ethanol / Heating 7: 3N HCl / Heating View Scheme

1.1: N-bromosuccinmide; acetic acid / water; tert-butyl alcohol / 1 h / 10 °C / |Inert atmosphere; |Large scale 2.1: sodium hydroxide / toluene; tert-butyl methyl ether / 78 °C / |Inert atmosphere; |Large scale 2.2: 1 h / 38 - 42 °C / |Large scale 3.1: sodium tetrahydroborate; cobalt(II) chloride; dmgH2; sodium hydroxide / water; tetrahydrofuran / 0.5 h / 15 - 20 °C 3.2: 15 - 20 °C / pH Ca. 10 View Scheme

1: 96 percent / MCPBA / methanol; CH2Cl2 / Ambient temperature 2: 1.) trifluoroacetic anhydride, 2.) aq. NaHCO3 / 1.) CH2Cl2, reflux, 2 h, 2.) THF View Scheme

1: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 2: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 3: 70percent m-chloroperbenzoic acid / methanol / Heating 4: 80 °C 5: NaOAc / ethanol / Heating 6: 3N HCl / Heating View Scheme

1: 63 percent / NaH / dimethylformamide 2: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 3: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 4: 70percent m-chloroperbenzoic acid / methanol / Heating 5: 80 °C 6: NaOAc / ethanol / Heating 7: 3N HCl / Heating View Scheme

1.1: zinc; acetic acid / 15 h / 25 - 30 °C 2.1: N-bromosuccinmide / tert-butyl alcohol; water / 1.5 h / 25 °C / |Large scale 2.2: 0.75 h / |Large scale 2.3: PEG 4000 / 17 h / 78 °C / |Large scale 3.1: pyrrolidine / methanol / 2 h / 50 - 55 °C / |Large scale 4.1: sodium tetrahydroborate; dmgH2; CoCl2.6H2O / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / |Large scale View Scheme

1.1: potassium hydroxide 2.1: N-bromosuccinmide; acetic acid / water; tert-butyl alcohol / 1 h / 10 °C / |Inert atmosphere; |Large scale 3.1: sodium hydroxide / toluene; tert-butyl methyl ether / 78 °C / |Inert atmosphere; |Large scale 3.2: 1 h / 38 - 42 °C / |Large scale 4.1: sodium tetrahydroborate; cobalt(II) chloride; dmgH2; sodium hydroxide / water; tetrahydrofuran / 0.5 h / 15 - 20 °C 4.2: 15 - 20 °C / pH Ca. 10 View Scheme

1.1: potassium carbonate / tert-butyl alcohol / 1.17 h / |Reflux 1.2: 11 h / |Reflux 2.1: pyrrolidine / methanol / 2 h / 50 - 55 °C / |Large scale 3.1: sodium tetrahydroborate; dmgH2; CoCl2.6H2O / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / |Large scale View Scheme

1.1: potassium carbonate / tert-butyl alcohol / 1.17 h / |Reflux 1.2: 11 h / |Reflux 2.1: pyrrolidine / methanol / 2 h / 50 - 55 °C / |Large scale 3.1: sodium tetrahydroborate; dmgH2; CoCl2.6H2O / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / |Large scale View Scheme