hydrogen; palladium dihydroxide in methanol T=20°C; 4 h;

1.1: H2 / PtO2 / ethanol / 1.5 h / 20 °C / 760.05 Torr 2.1: TMSOTf; 4 Angstroem MS / CH2Cl2 / 0.08 h / 20 °C 3.1: TMSOTf / acetonitrile / 17.5 h / -20 °C 4.1: 76 percent / m-CPBA / CH2Cl2 / 18.5 h / 20 °C 5.1: 69 percent / KOH / methanol / 32.5 h / Heating 6.1: Dess-Martin periodinane / CH2Cl2 / 4 h / 20 °C 6.2: 73 percent / triethylsilane; TMSOTf / acetonitrile / 0.25 h / 0 °C 7.1: 81 percent / aq. HCl / 2 h / Heating View Scheme

hydrogenchloride 2 h; Heating;

1: 62 percent / baker's yeast; sucrose; K2CO3 / H2O; ethanol / 90 h / 15 °C 2: 87 percent / NBS / acetonitrile / 0.5 h / 20 °C 3: potassium tert-butoxide / tetrahydrofuran / 0.25 h / 20 °C 4: 2.17 g / NBS / tetrahydrofuran / 1 h / 20 °C 5: aq. HCl / acetonitrile / 1 h / 20 °C 6: 1.58 g / K2CO3 / dimethylformamide / 1 h / 20 °C 7: 62 percent / H2 / Pd(OH)2/C / methanol / 4 h / 20 °C View Scheme

1: 87 percent / NBS / acetonitrile / 0.5 h / 20 °C 2: potassium tert-butoxide / tetrahydrofuran / 0.25 h / 20 °C 3: 2.17 g / NBS / tetrahydrofuran / 1 h / 20 °C 4: aq. HCl / acetonitrile / 1 h / 20 °C 5: 1.58 g / K2CO3 / dimethylformamide / 1 h / 20 °C 6: 62 percent / H2 / Pd(OH)2/C / methanol / 4 h / 20 °C View Scheme

1: potassium tert-butoxide / tetrahydrofuran / 0.25 h / 20 °C 2: 2.17 g / NBS / tetrahydrofuran / 1 h / 20 °C 3: aq. HCl / acetonitrile / 1 h / 20 °C 4: 1.58 g / K2CO3 / dimethylformamide / 1 h / 20 °C 5: 62 percent / H2 / Pd(OH)2/C / methanol / 4 h / 20 °C View Scheme

1: aq. HCl / acetonitrile / 1 h / 20 °C 2: 1.58 g / K2CO3 / dimethylformamide / 1 h / 20 °C 3: 62 percent / H2 / Pd(OH)2/C / methanol / 4 h / 20 °C View Scheme

hydrogenchloride; water 2.5 h; Reflux;

1.1: TMSOTf / acetonitrile / 17.5 h / -20 °C 2.1: 76 percent / m-CPBA / CH2Cl2 / 18.5 h / 20 °C 3.1: 69 percent / KOH / methanol / 32.5 h / Heating 4.1: Dess-Martin periodinane / CH2Cl2 / 4 h / 20 °C 4.2: 73 percent / triethylsilane; TMSOTf / acetonitrile / 0.25 h / 0 °C 5.1: 81 percent / aq. HCl / 2 h / Heating View Scheme

1.1: 69 percent / KOH / methanol / 32.5 h / Heating 2.1: Dess-Martin periodinane / CH2Cl2 / 4 h / 20 °C 2.2: 73 percent / triethylsilane; TMSOTf / acetonitrile / 0.25 h / 0 °C 3.1: 81 percent / aq. HCl / 2 h / Heating View Scheme