oxygen; dimethyl amine; copper dichloride 20 h;

hydrogen bromide T=140°C; 0.833333 h;

1: (i) SeO2, AcOH, (ii) 1,2-dimethoxy-ethane, H2SO4 2: O2, Me2NH / CuCl2 / dimethylformamide View Scheme

toluene-4-sulfonic acid in toluene 3.5 h; Heating;

1: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight 2: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 3: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 4: CCl4 / Heating 5: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 6: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h 7: 41 percent / O2, cupric chloride, dimethylamine / dimethylformamide; H2O View Scheme

1: H2SO4 / 9 °C 2: aq. H2O2, KOtBu View Scheme

palladium diacetate; potassium acetate in acetonitrile

1.1: 99 percent / H2 / Pd/C / ethyl acetate / 48 h / 20 °C 2.1: 98 percent / pyridine / 7 h / 3 °C 3.1: 83 percent / 4 Angstroem molecular sieves; tetrabutylammonium acetate; Pd(OAc)2 / acetonitrile / 10 h / 80 °C 4.1: O3; pyridine / CH2Cl2 / -100 °C 4.2: Me2S / CH2Cl2 / 1.5 h / -100 - 20 °C 5.1: NaBH4 / CH2Cl2 / 6 h / -60 - -50 °C 6.1: 62 percent / SeO2 / dioxane / 10 h / Heating 7.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 5 h / 20 °C 8.1: 93.7 mg / p-TsOH*H2O / toluene / 3 h / Heating 9.1: 86 percent / aq. HBr / 0.83 h / 140 °C View Scheme

1: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 2: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 3: CCl4 / Heating 4: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 5: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h 6: 41 percent / O2, cupric chloride, dimethylamine / dimethylformamide; H2O View Scheme

1: 93 percent / p-toluenesulfonic acid / toluene / 20 h / Heating 2: 1.) KH, ethanol, 2.) diethyl carbonate / 1.) toluene, reflux, 10 min, 2.) toluene, reflux, 3 h 3: 1.) potassium tert-butoxide / 1.) DME, -78 deg C, 5 min, 2.) DME, a.) -78 deg C, 1.5 h, b.) RT, overnight 4: 100 percent / H2 / Raney nickel / acetic acid / 6 h / 45 °C / 2585.7 Torr 5: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 6: CCl4 / Heating 7: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 8: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h 9: 41 percent / O2, cupric chloride, dimethylamine / dimethylformamide; H2O View Scheme