dipyridinium dichromate 1.) CH2Cl2, room temp., 12 h, 2.) CH2Cl2, Et2O, r.t., 2 h;

1: base 2: hydrogenating agent 3: 83 percent / acetic acid / Ambient temperature 4: 86 percent / 1M NaOH / H2O / 1 h / 10 °C 5: 100 percent / dioxane; diethyl ether 6: 95 percent / PDC / 1.) CH2Cl2, room temp., 12 h, 2.) CH2Cl2, Et2O, r.t., 2 h View Scheme

1: 1.) NaBH4/BF3*Et2O, 2.) 30percent H2O2/6M NaOH / 1.) diglyme, 20 deg C, 1h, 2.) diglyme, water, reflux, 1 h 2: 92 percent / Jones reagent / acetone / 1 h / 0 °C 3: 83 percent / acetic acid / Ambient temperature 4: 86 percent / 1M NaOH / H2O / 1 h / 10 °C 5: 100 percent / dioxane; diethyl ether 6: 95 percent / PDC / 1.) CH2Cl2, room temp., 12 h, 2.) CH2Cl2, Et2O, r.t., 2 h View Scheme

1: 92 percent / Jones reagent / acetone / 1 h / 0 °C 2: 83 percent / acetic acid / Ambient temperature 3: 86 percent / 1M NaOH / H2O / 1 h / 10 °C 4: 100 percent / dioxane; diethyl ether 5: 95 percent / PDC / 1.) CH2Cl2, room temp., 12 h, 2.) CH2Cl2, Et2O, r.t., 2 h View Scheme

1: 83 percent / acetic acid / Ambient temperature 2: 86 percent / 1M NaOH / H2O / 1 h / 10 °C 3: 100 percent / dioxane; diethyl ether 4: 95 percent / PDC / 1.) CH2Cl2, room temp., 12 h, 2.) CH2Cl2, Et2O, r.t., 2 h View Scheme

1: 86 percent / 1M NaOH / H2O / 1 h / 10 °C 2: 100 percent / dioxane; diethyl ether 3: 95 percent / PDC / 1.) CH2Cl2, room temp., 12 h, 2.) CH2Cl2, Et2O, r.t., 2 h View Scheme

1: 100 percent / dioxane; diethyl ether 2: 95 percent / PDC / 1.) CH2Cl2, room temp., 12 h, 2.) CH2Cl2, Et2O, r.t., 2 h View Scheme

1: hydrogenating agent 2: 83 percent / acetic acid / Ambient temperature 3: 86 percent / 1M NaOH / H2O / 1 h / 10 °C 4: 100 percent / dioxane; diethyl ether 5: 95 percent / PDC / 1.) CH2Cl2, room temp., 12 h, 2.) CH2Cl2, Et2O, r.t., 2 h View Scheme