1: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 2: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 3: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 5: 89 percent / 10percent HCl / tetrahydrofuran / 4 h / 25 °C View Scheme

1: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 2: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h View Scheme

1: 88 percent / 4.5 N aq. HCl / 12 h / Heating 2: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 3: 42.55 g / diisobutylaluminum hydride / toluene / 0.25 h / -78 - -70 °C 4: pyridinium chlorochromate / CH2Cl2 / 0.5 h / 25 °C View Scheme

1: 88 percent / 4.5 N aq. HCl / 12 h / Heating 2: oxalyl chloride / CH2Cl2 / 3 h / 25 °C View Scheme

1: 88 percent / 4.5 N aq. HCl / 12 h / Heating 2: 1.) acetyl chloride / 1.) 0 deg C, 0.25 h, 2.) reflux, 4 h 3: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 4: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h 5: 56 percent / manganese dioxide / CH2Cl2 / 40 h / 25 °C 6: 40 percent / N-bromosuccinimide / CCl4 / 0.5 h / Irradiation 7: 58 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / 18 h / 25 °C 8: 88 percent / sodium borohydride / methanol / 0.5 h / 0 °C 9: 10percent aq. NaOH / ethanol / 14 h / Heating View Scheme

ammonium chloride; magnesium in tetrahydrofuran

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in tetrahydrofuran; water T=60°C; Suzuki coupling; 6 h; Inert atmosphere;

1: thionyl chloride / 1 h / 25 °C 2: tetrahydrofuran / 2 h / 20 °C View Scheme

1: 95 percent / thionyl chloride / 18 h / 20 °C 2: CH2Cl2 / 2 h / 20 °C 3: thionyl chloride / 1 h / 25 °C 4: tetrahydrofuran / 2 h / 20 °C View Scheme

1: CH2Cl2 / 2 h / 20 °C 2: thionyl chloride / 1 h / 25 °C 3: tetrahydrofuran / 2 h / 20 °C View Scheme