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: 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 View Scheme