hydrogen; Raney-Ni (W4) in ethanol T=25°C; 1 h;

formic acid; water; sodium hydrogensulfite in ethanol 8 h; Heating;

ammonia in dichloromethane T=25°C;

1: 87 percent / DL-10-camphorsulfonic acid / CH2Cl2 / 72 h / -30 °C 2: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 1.5 h / 25 °C 3: 95 percent / H2 / Pd(OH)2/C / ethyl acetate / 2 h / 25 °C 4: 63 percent / silver triflate, 4A molecular sieves / CH2Cl2; toluene / 4 h / 25 °C 5: 100 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.25 h / 25 °C 6: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 7: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 8: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 9: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 10: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 11: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme

1: 63 percent / silver triflate, 4A molecular sieves / CH2Cl2; toluene / 4 h / 25 °C 2: 100 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.25 h / 25 °C 3: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 4: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 5: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 6: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 7: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 8: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme

1: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 1.5 h / 25 °C 2: 95 percent / H2 / Pd(OH)2/C / ethyl acetate / 2 h / 25 °C 3: 63 percent / silver triflate, 4A molecular sieves / CH2Cl2; toluene / 4 h / 25 °C 4: 100 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.25 h / 25 °C 5: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 6: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 7: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 8: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 9: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 10: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme

1: 95 percent / H2 / Pd(OH)2/C / ethyl acetate / 2 h / 25 °C 2: 63 percent / silver triflate, 4A molecular sieves / CH2Cl2; toluene / 4 h / 25 °C 3: 100 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.25 h / 25 °C 4: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 5: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 6: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 7: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 8: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 9: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme

1: 100 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.25 h / 25 °C 2: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 3: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 4: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 5: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 6: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 7: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme

1: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 2: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 3: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 4: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 5: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 6: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme

1: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 2: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme