sodium hydroxide in tetrahydrofuran; methanol; water T=50°C; 2 h;

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: 100 percent / 4A molecular sieves; BF3*OEt2 / CH2Cl2 / 1 h / -40 °C 2: 80 percent / TsOH*H2O / methanol; CH2Cl2 / 2 h / 20 °C 3: 75 percent / pyridine / CH2Cl2 / -20 °C 4: 93 percent / 4A molecular sieves; BF3*OEt2 / CH2Cl2 / 0.5 h / 0 °C 5: 85 percent / NaOH; H2O / tetrahydrofuran / 45 °C View Scheme

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

1: 75 percent / pyridine / CH2Cl2 / -20 °C 2: 93 percent / 4A molecular sieves; BF3*OEt2 / CH2Cl2 / 0.5 h / 0 °C 3: 85 percent / NaOH; H2O / tetrahydrofuran / 45 °C View Scheme

1: 80 percent / TsOH*H2O / methanol; CH2Cl2 / 2 h / 20 °C 2: 75 percent / pyridine / CH2Cl2 / -20 °C 3: 93 percent / 4A molecular sieves; BF3*OEt2 / CH2Cl2 / 0.5 h / 0 °C 4: 85 percent / NaOH; H2O / tetrahydrofuran / 45 °C View Scheme

1: 93 percent / 4A molecular sieves; BF3*OEt2 / CH2Cl2 / 0.5 h / 0 °C 2: 85 percent / NaOH; H2O / tetrahydrofuran / 45 °C View Scheme

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

1: 100 percent / HBr; HOAc / CH2Cl2 / 20 °C 2: 100 percent / DBU / CH2Cl2 / 0.5 h / 0 °C 3: 93 percent / 4A molecular sieves; BF3*OEt2 / CH2Cl2 / 0.5 h / 0 °C 4: 85 percent / NaOH; H2O / tetrahydrofuran / 45 °C View Scheme

1: 100 percent / 4A molecular sieves; BF3*OEt2 / CH2Cl2 / 1 h / -40 °C 2: 80 percent / TsOH*H2O / methanol; CH2Cl2 / 2 h / 20 °C 3: 75 percent / pyridine / CH2Cl2 / -20 °C 4: 93 percent / 4A molecular sieves; BF3*OEt2 / CH2Cl2 / 0.5 h / 0 °C 5: 85 percent / NaOH; H2O / tetrahydrofuran / 45 °C View Scheme