1: 50 percent / 4A molecular sieves; NIS; AgOTf / CH2Cl2; toluene / 1 h / -30 °C 2: 85 percent / NaOMe / methanol; CH2Cl2 / 50 °C / pH 15 3: 64 percent / pyridine / 2 h / 20 °C 4: 100 percent / 4A molecular sieves; BF3*OEt2 / CH2Cl2 / 1 h / -40 °C 5: 80 percent / TsOH*H2O / methanol; CH2Cl2 / 2 h / 20 °C 6: 75 percent / pyridine / CH2Cl2 / -20 °C 7: 93 percent / 4A molecular sieves; BF3*OEt2 / CH2Cl2 / 0.5 h / 0 °C 8: 85 percent / NaOH; H2O / tetrahydrofuran / 45 °C View Scheme

1: 50 percent / 4A molecular sieves; NIS; AgOTf / CH2Cl2; toluene / 1 h / -30 °C 2: 85 percent / NaOMe / methanol; CH2Cl2 / 50 °C / pH 15 3: 64 percent / pyridine / 2 h / 20 °C 4: 100 percent / 4A molecular sieves; BF3*OEt2 / CH2Cl2 / 1 h / -40 °C 5: 80 percent / TsOH*H2O / methanol; CH2Cl2 / 2 h / 20 °C 6: 75 percent / pyridine / CH2Cl2 / -20 °C 7: 89 percent / 4A molecular sieves; BF3*OEt2 / CH2Cl2 / 1 h / -40 °C 8: 100 percent / NaOH; water / methanol; tetrahydrofuran / 5 h / 45 °C View Scheme