1: hydrogen / platinum / methanol; ethyl acetate 2: 85 percent / p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 24 h 3: 92 percent / 4-dimethylaminopyridine / tetrahydrofuran / 24 h View Scheme

1: 91 percent / triethylamine 2: 98 percent / sodium borohydride, lithium chloride / tetrahydrofuran; ethanol 3: 100 percent / H2 / Rh-Al2O3 / acetic acid; methanol / 5 h / 3040 Torr / Ambient temperature 4: 78 percent / sulfur trioxide pyridine, triethylamine, dimethylsulfoxide / toluene / 0.33 h / Ambient temperature 5: TiCl4, molecular sieves / CH2Cl2 / 1 h / -78 °C 6: 93 percent / aq. HCl / ethyl acetate / 13 h / 100 °C View Scheme

1: 78 percent / sulfur trioxide pyridine, triethylamine, dimethylsulfoxide / toluene / 0.33 h / Ambient temperature 2: TiCl4, molecular sieves / CH2Cl2 / 1 h / -78 °C 3: 93 percent / aq. HCl / ethyl acetate / 13 h / 100 °C View Scheme

1: TiCl4, molecular sieves / CH2Cl2 / 1 h / -78 °C 2: 93 percent / aq. HCl / ethyl acetate / 13 h / 100 °C View Scheme

1: 70 percent / NaN(SiMe3)2 / tetrahydrofuran / -78 °C 2: 1.) DIBAH; 2.) DMAP, Et3N / 1.) CH2Cl2, -78 degC; 2.) CH2Cl2 3: ZnBr2 / CH2Cl2 / from -45 degC to 0 degC 4: 1.) KOH; 2.) Li / 1.) dioxane, MeOH; 2.) NH3, THF, t-BuOH View Scheme

1: 1.) DIBAH; 2.) DMAP, Et3N / 1.) CH2Cl2, -78 degC; 2.) CH2Cl2 2: ZnBr2 / CH2Cl2 / from -45 degC to 0 degC 3: 1.) KOH; 2.) Li / 1.) dioxane, MeOH; 2.) NH3, THF, t-BuOH View Scheme

1: 85 percent / p-toluenesulfonic acid / CH2Cl2; tetrahydrofuran / 24 h 2: 92 percent / 4-dimethylaminopyridine / tetrahydrofuran / 24 h View Scheme

1: 92 percent / 4-dimethylaminopyridine / tetrahydrofuran / 24 h View Scheme

potassium hydroxide; lithium 1.) dioxane, MeOH; 2.) NH3, THF, t-BuOH; Yield given. Multistep reaction;

Yield given. Multistep reaction;