1: 1.) pyridinium dichromate / 1.) DMF, 40 deg C, 48 h 2: 64 percent / 60percent AcOH / 24 h / 60 °C 3: t-AmONa / benzene / 0.5 h / Ambient temperature 4: Et3N / tetrahydrofuran; H2O / 1 h / Ambient temperature 5: 3 percent / O3 / CH2Cl2 / -78 °C 6: 60 percent / n-BuLi / tetrahydrofuran / -78 deg C, 2 min -> 0 deg C, 1 h 7: Jones reagent 8: KOH / 24 h / Ambient temperature View Scheme

1: t-AmONa / benzene / 0.5 h / Ambient temperature 2: Et3N / tetrahydrofuran; H2O / 1 h / Ambient temperature 3: 3 percent / O3 / CH2Cl2 / -78 °C 4: 60 percent / n-BuLi / tetrahydrofuran / -78 deg C, 2 min -> 0 deg C, 1 h 5: Jones reagent 6: KOH / 24 h / Ambient temperature View Scheme

1: MeOH - p-TsOH / 3 h / Ambient temperature 2: 1.) pyridinium dichromate / 1.) DMF, 40 deg C, 48 h 3: 64 percent / 60percent AcOH / 24 h / 60 °C 4: t-AmONa / benzene / 0.5 h / Ambient temperature 5: Et3N / tetrahydrofuran; H2O / 1 h / Ambient temperature 6: 3 percent / O3 / CH2Cl2 / -78 °C 7: 60 percent / n-BuLi / tetrahydrofuran / -78 deg C, 2 min -> 0 deg C, 1 h 8: Jones reagent 9: KOH / 24 h / Ambient temperature View Scheme

1: Et3N / tetrahydrofuran; H2O / 1 h / Ambient temperature 2: 3 percent / O3 / CH2Cl2 / -78 °C 3: 60 percent / n-BuLi / tetrahydrofuran / -78 deg C, 2 min -> 0 deg C, 1 h 4: Jones reagent 5: KOH / 24 h / Ambient temperature View Scheme

1: 64 percent / 60percent AcOH / 24 h / 60 °C 2: t-AmONa / benzene / 0.5 h / Ambient temperature 3: Et3N / tetrahydrofuran; H2O / 1 h / Ambient temperature 4: 3 percent / O3 / CH2Cl2 / -78 °C 5: 60 percent / n-BuLi / tetrahydrofuran / -78 deg C, 2 min -> 0 deg C, 1 h 6: Jones reagent 7: KOH / 24 h / Ambient temperature View Scheme

1: 3 percent / O3 / CH2Cl2 / -78 °C 2: 60 percent / n-BuLi / tetrahydrofuran / -78 deg C, 2 min -> 0 deg C, 1 h 3: Jones reagent 4: KOH / 24 h / Ambient temperature View Scheme

1: 60 percent / n-BuLi / tetrahydrofuran / -78 deg C, 2 min -> 0 deg C, 1 h 2: Jones reagent 3: KOH / 24 h / Ambient temperature View Scheme

1: 70 percent / BH3-DMS 2: MeOH - p-TsOH / 3 h / Ambient temperature 3: 1.) pyridinium dichromate / 1.) DMF, 40 deg C, 48 h 4: 64 percent / 60percent AcOH / 24 h / 60 °C 5: t-AmONa / benzene / 0.5 h / Ambient temperature 6: Et3N / tetrahydrofuran; H2O / 1 h / Ambient temperature 7: 3 percent / O3 / CH2Cl2 / -78 °C 8: 60 percent / n-BuLi / tetrahydrofuran / -78 deg C, 2 min -> 0 deg C, 1 h 9: Jones reagent 10: KOH / 24 h / Ambient temperature View Scheme

potassium hydroxide 24 h; Ambient temperature;

1: Jones reagent 2: KOH / 24 h / Ambient temperature View Scheme