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

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

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

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

Multi-step reaction with 3 steps 1: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h2: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C3: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature  

Multi-step reaction with 6 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 °C5: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature6: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C  

Multi-step reaction with 6 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 °C5: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature6: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C  

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 5 steps 1: H2 / 10percent Pd/C / tetrahydrofuran / 760 Torr / Ambient temperature2: p-TsOH, / CHCl3 / Ambient temperature3: Jones' reagent / acetone / 1 h / 10 °C4: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature5: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C  

Multi-step reaction with 5 steps 1: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature2: benzenesulfonylchloride, pyridine / 0 °C3: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C4: 1.) 1 N KOH, 2.) p-TsOH / 1.) dioxane, water, RT, overnight, 2.) chloroform, RT, 2 h5: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C