1: 1.) NaBH4, 2.) 10percent aq. H2SO4, HOCH2CH2OH / 2.) heating 3: 70 percent / Cu, K2CO3 / Heating 4: 90 percent / 3N aq. HCl 5: 25 percent / Pd(OAc)2 / trifluoroacetic acid; acetic acid View Scheme

1.1: 66 percent / HNO3 / H2O / 0.08 h / -20 °C 2.1: 99 percent / NaBH4 / methanol / 0.17 h / 0 °C 3.1: 86 percent / TsOH / benzene / 16 h / Heating 4.1: O3 / CH2Cl2; methanol / -78 °C 4.2: Me2S; NaHCO3 / CH2Cl2; methanol / 4 h / 20 °C 4.3: 89 percent / NH3 / CH2Cl2; methanol; H2O / 16 h 5.1: 94 percent / NaOMe / dimethylformamide / 6 h / Heating 6.1: hydrazine monohydrate; Raney nickel / H2O; ethanol / 2 h / Heating 7.1: 34 percent / HOAc; NaNO2 / H2O / 0 - 20 °C View Scheme