1: 90 percent / NaOH / dioxane / 14 h / 100 °C 2: p-toluenesulfonic acid, H2O / methanol / 8 h / Ambient temperature 3: 100 percent / K2CO3 / acetone / 1 h / Heating 4: 98 percent / H2 / 10percent Pd-C / acetic acid / 0.5 h View Scheme

1: 90 percent / NaOH / dioxane / 14 h / 100 °C 2: p-toluenesulfonic acid, H2O / methanol / 8 h / Ambient temperature 3: 100 percent / K2CO3 / acetone / 1 h / Heating 4: 98 percent / H2 / 10percent Pd-C / acetic acid / 0.5 h 5: 78 percent / K2(SO3)2NO, aq. NaOAc / benzene View Scheme

1: 1.) NaH, 2.) DMAP / 1.) THF, 0 deg C, 2.) THF, 0 deg C to room temp., 20 h 2: 70 percent / K2CO3, CuO / dimethylformamide / 1.5 h / Heating 3: 58 percent / TMEDA, sec-BuLi / tetrahydrofuran; cyclohexane / -78 deg C to room temp., then overnight View Scheme

1: 90 percent / NaOH / dioxane / 14 h / 100 °C 2: p-toluenesulfonic acid, H2O / methanol / 8 h / Ambient temperature View Scheme