1: 1) mCPBA, 2) 2N HCl / 1) CH2Cl2, -30 to -25 deg C, 20 h, 2) THF, RT, 16 h 2: Me4NBH(OAc)3 / acetic acid; acetonitrile / 2 h / 0 °C 3: DDQ / dioxane / 4 h / 80 °C 4: 94 percent / Ag2O / acetonitrile / 24 h / Ambient temperature 5: 92 percent / MsCl, Et3N / CH2Cl2 / Ambient temperature 6: 47 percent / OsO4, DABCO / tetrahydrofuran / 24 h / -40 °C 7: 92 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 16 h / Ambient temperature 8: CH(NMe2)3 / 1 h / 100 °C 9: 2N HCl / tetrahydrofuran / 20 h / Ambient temperature 10: PCC / CH2Cl2 / 5 h / Ambient temperature 11: CH2Cl2 / 0.33 h / Ambient temperature 12: DBN / CH2Cl2 / 6 h / Ambient temperature 13: K2CO3, MeOH / 5 h / Ambient temperature 14: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature 15: 49 percent / pyridine / 12 h / -20 °C 16: 73 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 94 percent / Ag2O / acetonitrile / 24 h / Ambient temperature 2: 92 percent / MsCl, Et3N / CH2Cl2 / Ambient temperature 3: 47 percent / OsO4, DABCO / tetrahydrofuran / 24 h / -40 °C 4: 92 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 16 h / Ambient temperature 5: CH(NMe2)3 / 1 h / 100 °C 6: 2N HCl / tetrahydrofuran / 20 h / Ambient temperature 7: PCC / CH2Cl2 / 5 h / Ambient temperature 8: CH2Cl2 / 0.33 h / Ambient temperature 9: DBN / CH2Cl2 / 6 h / Ambient temperature 10: K2CO3, MeOH / 5 h / Ambient temperature 11: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature 12: 49 percent / pyridine / 12 h / -20 °C 13: 73 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 47 percent / OsO4, DABCO / tetrahydrofuran / 24 h / -40 °C 2: 92 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 16 h / Ambient temperature 3: CH(NMe2)3 / 1 h / 100 °C 4: 2N HCl / tetrahydrofuran / 20 h / Ambient temperature 5: PCC / CH2Cl2 / 5 h / Ambient temperature 6: CH2Cl2 / 0.33 h / Ambient temperature 7: DBN / CH2Cl2 / 6 h / Ambient temperature 8: K2CO3, MeOH / 5 h / Ambient temperature 9: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature 10: 49 percent / pyridine / 12 h / -20 °C 11: 73 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 92 percent / MsCl, Et3N / CH2Cl2 / Ambient temperature 2: 47 percent / OsO4, DABCO / tetrahydrofuran / 24 h / -40 °C 3: 92 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 16 h / Ambient temperature 4: CH(NMe2)3 / 1 h / 100 °C 5: 2N HCl / tetrahydrofuran / 20 h / Ambient temperature 6: PCC / CH2Cl2 / 5 h / Ambient temperature 7: CH2Cl2 / 0.33 h / Ambient temperature 8: DBN / CH2Cl2 / 6 h / Ambient temperature 9: K2CO3, MeOH / 5 h / Ambient temperature 10: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature 11: 49 percent / pyridine / 12 h / -20 °C 12: 73 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme

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

1: CH2Cl2 / 0.17 h / Ambient temperature 2: K2CO3, MeOH / 5 h / Ambient temperature 3: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature 4: 49 percent / pyridine / 12 h / -20 °C 5: 73 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: CH(NMe2)3 / 1 h / 100 °C 2: 2N HCl / tetrahydrofuran / 20 h / Ambient temperature 3: PCC / CH2Cl2 / 5 h / Ambient temperature 4: CH2Cl2 / 0.33 h / Ambient temperature 5: DBN / CH2Cl2 / 6 h / Ambient temperature 6: K2CO3, MeOH / 5 h / Ambient temperature 7: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature 8: 49 percent / pyridine / 12 h / -20 °C 9: 73 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: CH2Cl2 / 0.33 h / Ambient temperature 2: DBN / CH2Cl2 / 6 h / Ambient temperature 3: K2CO3, MeOH / 5 h / Ambient temperature 4: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature 5: 49 percent / pyridine / 12 h / -20 °C 6: 73 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 92 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 16 h / Ambient temperature 2: CH(NMe2)3 / 1 h / 100 °C 3: 2N HCl / tetrahydrofuran / 20 h / Ambient temperature 4: PCC / CH2Cl2 / 5 h / Ambient temperature 5: CH2Cl2 / 0.33 h / Ambient temperature 6: DBN / CH2Cl2 / 6 h / Ambient temperature 7: K2CO3, MeOH / 5 h / Ambient temperature 8: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature 9: 49 percent / pyridine / 12 h / -20 °C 10: 73 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme

phosphate buffer in dimethyl sulfoxide T=37°C; pH=6.8; Kinetics; Further Variations:Solvents;