1: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature 2: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C 3: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h 4: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C 5: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 6: benzenesulfonylchloride, pyridine / 0 °C 7: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C View Scheme

1: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature 2: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C 3: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h 4: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C 5: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 6: benzenesulfonylchloride, pyridine / 0 °C 7: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C 8: 80 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature 2: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C 3: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h 4: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C 5: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 6: benzenesulfonylchloride, pyridine / 0 °C 7: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C View Scheme

hydrogen; platinum in ethyl acetate T=20°C; P=34202.3 Torr; 48 h;

Multi-step reaction with 5 steps 1: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature2: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C3: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h4: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C5: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature  

Multi-step reaction with 3 steps 1: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature2: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C3: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h  

Multi-step reaction with 2 steps 1: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature2: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C  

Multi-step reaction with 4 steps 1: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature2: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C3: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h4: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C  

Multi-step reaction with 4 steps 1: 1.) diisopropylamine, BuLi / 1.) THF, hexane, a) -50 deg C, 15 min, b) RT, 1 h, 2.) -78 deg C, 3 h2: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr / Ambient temperature3: p-TsOH, / CHCl3 / Ambient temperature4: Jones' reagent / acetone / 1 h / 10 °C  

Multi-step reaction with 4 steps 1: 1.) diisopropylamine, BuLi / 1.) THF, hexane, a) -50 deg C, 15 min, b) RT, 1 h, 2.) -78 deg C, 3 h2: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr / Ambient temperature3: p-TsOH, / CHCl3 / Ambient temperature4: Jones' reagent / acetone / 1 h / 10 °C