1: 80 percent / KOH / butan-2-one / 15 h / Heating 2: 73 percent / potassium tert-butoxide / dimethylsulfoxide / 96 h / 60 °C 3: sodium metaperiodate, OsO4 / dioxane; H2O / 120 h / 25 °C 4: 33 percent / p-toluenesilfonic acid / toluene / 8 h / 80 °C View Scheme

1: sodium metaperiodate, OsO4 / dioxane; H2O / 120 h / 25 °C 2: 33 percent / p-toluenesilfonic acid / toluene / 8 h / 80 °C View Scheme

1: 73 percent / potassium tert-butoxide / dimethylsulfoxide / 96 h / 60 °C 2: sodium metaperiodate, OsO4 / dioxane; H2O / 120 h / 25 °C 3: 33 percent / p-toluenesilfonic acid / toluene / 8 h / 80 °C View Scheme

1: 2.) NaOAc, HOAc / 1.) toluene, 50 deg C, 72 h, 2.) reflux, 30 min 2: 80 percent / KOH / butan-2-one / 15 h / Heating 3: 73 percent / potassium tert-butoxide / dimethylsulfoxide / 96 h / 60 °C 4: sodium metaperiodate, OsO4 / dioxane; H2O / 120 h / 25 °C 5: 33 percent / p-toluenesilfonic acid / toluene / 8 h / 80 °C View Scheme