samarium; iodine in methanol 6 h; Heating;

dihydrogen peroxide; trifluoroacetic anhydride in dichloromethane T=0 - 20°C;

PPA T=160°C; 5 h;

dipotassium peroxodisulfate; silver(I) acetate in acetonitrile-D3 T=130°C; Pschorr reaction; 1 h; Microwave irradiation;

sulfuric acid

1: 2.) 2 M aq. Na2CO3 / 1.) Pd(PPh3)4 / 1.) EtOH, DME, 10 min, 2.) reflux, 20 h 2: 94 percent / NBS / benzoyl peroxide / CCl4 / 36 h / Heating 3: AgNO3 / dioxane; H2O / 18 h / Ambient temperature 4: aq. KOH / dioxane / 20 h / Ambient temperature 5: 86 percent / aq. KMnO4 / acetone / 4 h / Ambient temperature 6: 62 percent / polyphosphoric acid / 5 h / 160 °C View Scheme

1: 2.) 2 M aq. Na2CO3 / 1.) Pd(PPh3)4 / 1.) EtOH, DME, 10 min, 2.) reflux, 20 h 2: 94 percent / NBS / benzoyl peroxide / CCl4 / 36 h / Heating 3: AgNO3 / dioxane; H2O / 18 h / Ambient temperature 4: aq. KOH / dioxane / 20 h / Ambient temperature 5: 86 percent / aq. KMnO4 / acetone / 4 h / Ambient temperature 6: 62 percent / polyphosphoric acid / 5 h / 160 °C View Scheme

1: H2SO4 / anschliessendes Behandeln mit wss. NaNO2 2: H2SO4 View Scheme

1: n-butyllithium / tetrahydrofuran / Cooling 2: dipotassium peroxodisulfate; silver(I) acetate / acetonitrile-D3 / 1 h / 130 °C / Microwave irradiation View Scheme

1: 86 percent / aq. KMnO4 / acetone / 4 h / Ambient temperature 2: 62 percent / polyphosphoric acid / 5 h / 160 °C View Scheme