1.1: titanium tetrachloride / 20 °C 1.2: 20 °C 2.1: sodium chlorite; potassium dihydrogenphosphate; dihydrogen peroxide / acetonitrile / 20 °C 2.2: 20 °C 3.1: boron tribromide / dichloromethane View Scheme

potassium carbonate in acetone 24 h; Heating / reflux;

potassium hydroxide in acetone Ambient temperature;

1: 88 percent / EtMgBr / tetrahydrofuran 3: H2 / 10percentPd-C / acetic acid; aq. HClO4 / 4 h / 60 °C / 2585.7 Torr 4: PPE / CH2Cl2 / 0.5 h / Heating 5: 1.) H2SO4, 2.) o-chloranil / 1.) toluene, reflux, 2h, 2.) reflux, 1h 6: 96 percent / NaBH4 / 1,2-dimethoxy-ethane / 3 h / Heating 7: 95 percent / 150 - 215 °C 8: 87 percent / KOH / acetone / Ambient temperature View Scheme

2: H2 / 10percentPd-C / acetic acid; aq. HClO4 / 4 h / 60 °C / 2585.7 Torr 3: PPE / CH2Cl2 / 0.5 h / Heating 4: 1.) H2SO4, 2.) o-chloranil / 1.) toluene, reflux, 2h, 2.) reflux, 1h 5: 96 percent / NaBH4 / 1,2-dimethoxy-ethane / 3 h / Heating 6: 95 percent / 150 - 215 °C 7: 87 percent / KOH / acetone / Ambient temperature View Scheme

1: H2 / 10percentPd-C / acetic acid; aq. HClO4 / 4 h / 60 °C / 2585.7 Torr 2: PPE / CH2Cl2 / 0.5 h / Heating 3: 1.) H2SO4, 2.) o-chloranil / 1.) toluene, reflux, 2h, 2.) reflux, 1h 4: 96 percent / NaBH4 / 1,2-dimethoxy-ethane / 3 h / Heating 5: 95 percent / 150 - 215 °C 6: 87 percent / KOH / acetone / Ambient temperature View Scheme

1: 95 percent / 150 - 215 °C 2: 87 percent / KOH / acetone / Ambient temperature View Scheme

1: palladium/charcoal; methanol; aqueous HCl / Hydrogenation 2: 215 °C 3: aqueous KOH; dioxane View Scheme

1: LiAlH4; diethyl ether 2: palladium/charcoal; methanol; aqueous HCl / Hydrogenation 3: 215 °C 4: aqueous KOH; dioxane View Scheme

1: 1.) H2SO4, 2.) o-chloranil / 1.) toluene, reflux, 2h, 2.) reflux, 1h 2: 96 percent / NaBH4 / 1,2-dimethoxy-ethane / 3 h / Heating 3: 95 percent / 150 - 215 °C 4: 87 percent / KOH / acetone / Ambient temperature View Scheme