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

1: Jones' reagent / acetone / 1 h / 10 °C 2: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature 3: 73 percent / CF3SO3H / CH2Cl2 / 2 h / 0 - 20 °C 4: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h 5: 73 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / -10 - 20 °C 6: H2 / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature 7: benzenesulfonylchloride, pyridine / 0 °C 8: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C 9: 80 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 2 h / Ambient temperature View Scheme

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

1: Jones' reagent / acetone / 1 h / 10 °C 2: 84 percent / H2 / PtO2 / ethyl acetate / 48 h / 37503 Torr / Ambient temperature View Scheme

toluene-4-sulfonic acid in chloroform 18 h; Heating;