1.1: 94 percent / Pd(OAc)2; Et3N; (2-MeC6H4)3P / acetonitrile / 24 h / Heating 2.1: 99 percent / 1 M aq. NaOH / dioxane / 2 h / 20 °C 3.1: H2 / 10 percent Pd/C / ethyl acetate / 70 °C / 3040 Torr 4.1: Et3N; DCC; HOBt / dimethylformamide / 5 h / 0 - 20 °C 5.1: conc. HCl / 8 h / Heating 5.2: H2O / pH 4 - 6 View Scheme

1.1: 1,2-dimethoxy-ethane / 2 h 1.2: I2 / tetrahydrofuran / 3 h / 20 °C 2.1: 94 percent / Pd(OAc)2; Et3N; (2-MeC6H4)3P / acetonitrile / 24 h / Heating 3.1: 99 percent / 1 M aq. NaOH / dioxane / 2 h / 20 °C 4.1: H2 / 10 percent Pd/C / ethyl acetate / 70 °C / 3040 Torr 5.1: Et3N; DCC; HOBt / dimethylformamide / 5 h / 0 - 20 °C 6.1: conc. HCl / 8 h / Heating 6.2: H2O / pH 4 - 6 View Scheme

1.1: 99 percent / 1 M aq. NaOH / dioxane / 2 h / 20 °C 2.1: H2 / 10 percent Pd/C / ethyl acetate / 70 °C / 3040 Torr 3.1: Et3N; DCC; HOBt / dimethylformamide / 5 h / 0 - 20 °C 4.1: conc. HCl / 8 h / Heating 4.2: H2O / pH 4 - 6 View Scheme

1: 100 percent / B(OMe)3, BMS / tetrahydrofuran / 72 h / Ambient temperature 2: 98 percent / PBr3 / CH2Cl2 / 16 h / Ambient temperature 3: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 5 min, 2.) THF, HMPA, hexane, a) -78 deg C, 15 min, 2.) RT, 2 h 4: 87 percent / 1N HCl / tetrahydrofuran / 4 h / 0 °C 5: LiOH, LiBr, n-Bu4NBr / acetonitrile / 1 h / Ambient temperature View Scheme

1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 5 min, 2.) THF, HMPA, hexane, a) -78 deg C, 15 min, 2.) RT, 2 h 2: 87 percent / 1N HCl / tetrahydrofuran / 4 h / 0 °C 3: LiOH, LiBr, n-Bu4NBr / acetonitrile / 1 h / Ambient temperature View Scheme

1: 98 percent / PBr3 / CH2Cl2 / 16 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 5 min, 2.) THF, HMPA, hexane, a) -78 deg C, 15 min, 2.) RT, 2 h 3: 87 percent / 1N HCl / tetrahydrofuran / 4 h / 0 °C 4: LiOH, LiBr, n-Bu4NBr / acetonitrile / 1 h / Ambient temperature View Scheme

1: 87 percent / 1N HCl / tetrahydrofuran / 4 h / 0 °C 2: LiOH, LiBr, n-Bu4NBr / acetonitrile / 1 h / Ambient temperature View Scheme