1: 71 percent / LTBA / tetrahydrofuran / -78 to -40 deg C; -35 deg C, 4 h 2: 89 percent / nBu3P / tetrahydrofuran / 1 h / 0 - 20 °C 3: 85 percent / 30percent H2O2 / tetrahydrofuran / 18 h / 0 - 20 °C 4: I2, NaHCO3 / CH2Cl2 / 48 h / Ambient temperature 5: 90 percent / methanol / 4 h / 0 - 20 °C 6: LTBA / tetrahydrofuran / 3 h / 0 °C 7: pyridine / 2 h / 0 - 20 °C 8: 56 percent / CSA, dihydroquinone / benzene / 3 h / Heating 9: 1) mCPBA, 2) 2N HCl / 1) CH2Cl2, -30 to -25 deg C, 20 h, 2) THF, RT, 16 h 10: Me4NBH(OAc)3 / acetic acid; acetonitrile / 2 h / 0 °C 11: DDQ / dioxane / 4 h / 80 °C 12: 94 percent / Ag2O / acetonitrile / 24 h / Ambient temperature 13: 92 percent / MsCl, Et3N / CH2Cl2 / Ambient temperature 14: 47 percent / OsO4, DABCO / tetrahydrofuran / 24 h / -40 °C 15: 92 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 16 h / Ambient temperature 16: CH(NMe2)3 / 1 h / 100 °C 17: 2N HCl / tetrahydrofuran / 20 h / Ambient temperature 18: PCC / CH2Cl2 / 5 h / Ambient temperature 19: CH2Cl2 / 0.33 h / Ambient temperature 20: DBN / CH2Cl2 / 6 h / Ambient temperature 21: K2CO3, MeOH / 5 h / Ambient temperature 22: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature 23: 49 percent / pyridine / 12 h / -20 °C 24: 73 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 71 percent / LTBA / tetrahydrofuran / -78 to -40 deg C; -35 deg C, 4 h 2: 89 percent / nBu3P / tetrahydrofuran / 1 h / 0 - 20 °C 3: 85 percent / 30percent H2O2 / tetrahydrofuran / 18 h / 0 - 20 °C 4: I2, NaHCO3 / CH2Cl2 / 48 h / Ambient temperature 5: 90 percent / methanol / 4 h / 0 - 20 °C 6: LTBA / tetrahydrofuran / 3 h / 0 °C 7: pyridine / 2 h / 0 - 20 °C 8: 56 percent / CSA, dihydroquinone / benzene / 3 h / Heating 9: 1) mCPBA, 2) 2N HCl / 1) CH2Cl2, -30 to -25 deg C, 20 h, 2) THF, RT, 16 h 10: Me4NBH(OAc)3 / acetic acid; acetonitrile / 2 h / 0 °C 11: DDQ / dioxane / 4 h / 80 °C 12: 94 percent / Ag2O / acetonitrile / 24 h / Ambient temperature 13: 92 percent / MsCl, Et3N / CH2Cl2 / Ambient temperature 14: 47 percent / OsO4, DABCO / tetrahydrofuran / 24 h / -40 °C 15: 92 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 16 h / Ambient temperature 16: CH(NMe2)3 / 1 h / 100 °C 17: 2N HCl / tetrahydrofuran / 20 h / Ambient temperature 18: PCC / CH2Cl2 / 5 h / Ambient temperature 19: CH2Cl2 / 0.33 h / Ambient temperature 20: DBN / CH2Cl2 / 6 h / Ambient temperature 21: K2CO3, MeOH / 5 h / Ambient temperature 22: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature 23: 49 percent / pyridine / 12 h / -20 °C View Scheme