CaCl2x2H2O; potassium hydroxide in methanol T=0°C; 8 h; Inert atmosphere;

acetic acid in water T=120°C; 0.166667 h;

diphosphorous tetraiodide in dichloromethane 0 degC, 25 min and room temp., 5 min;

1: 94 percent / CBr4, Ph3P / CH2Cl2 / 3 h / -78 - -60 °C 2: 26 percent / KOH / H2O / 0.67 h 3: 70 percent / acetic acid / H2O / 0.17 h / 120 °C View Scheme

1: 26 percent / KOH / H2O / 0.67 h 2: 70 percent / acetic acid / H2O / 0.17 h / 120 °C View Scheme

1: 90 percent / pyridine / Ambient temperature 2: 80.4 percent / Me3SiOTf / CH2Cl2 / 7 h / 0 - 5 °C 3: 93.1 percent / K2CO3 / methanol; H2O / Ambient temperature 4: 1.) n-BuLi, p-TsCl, HMPA; 2.) LiBr / 1.) n-hexane, ether, 0 deg C, 5 min; 2.) n-hexane, ether, RT, overnight 6: 63.2 percent / CaCO3, NCS / dimethylformamide; H2O / 0 - 25 °C 7: 50 percent / DBU / tetrahydrofuran / 4 h / Heating 8: 1.) EtMgBr / 1.) ether, RT, 30 min; 2.) 100 deg C, 10 min 9: 31.5 percent / AcOH / H2O / 0.5 h / Heating View Scheme

1: 15 percent / LiNPr2 / tetrahydrofuran 2: MsCl / pyridine 3: 96.1 percent / acetic acid; tetrahydrofuran; H2O / 2 h / 50 °C 4: 90 percent / pyridine / Ambient temperature 5: 80.4 percent / Me3SiOTf / CH2Cl2 / 7 h / 0 - 5 °C 6: 93.1 percent / K2CO3 / methanol; H2O / Ambient temperature 7: 1.) n-BuLi, p-TsCl, HMPA; 2.) LiBr / 1.) n-hexane, ether, 0 deg C, 5 min; 2.) n-hexane, ether, RT, overnight 9: 63.2 percent / CaCO3, NCS / dimethylformamide; H2O / 0 - 25 °C 10: 50 percent / DBU / tetrahydrofuran / 4 h / Heating 11: 1.) EtMgBr / 1.) ether, RT, 30 min; 2.) 100 deg C, 10 min 12: 31.5 percent / AcOH / H2O / 0.5 h / Heating View Scheme

1: 26 percent / KOH / H2O / 0.67 h 2: 70 percent / acetic acid / H2O / 0.17 h / 120 °C View Scheme

1: 1.) NaH, 2.) n-BuLi 2: 1.) NaH / 1.) ether, 0 deg C, 20 min, 2.) ether, RT, 1.5 h 3: 1.) CuI / 1.) ether, 0 deg C, 30 min, 2.) ether, -78 deg C, 3 h 4: 96 percent / diisobutylaluminum hydride / CH2Cl2 / 1 h / -78 °C 5: 94 percent / CBr4, Ph3P / CH2Cl2 / 3 h / -78 - -60 °C 6: 26 percent / KOH / H2O / 0.67 h 7: 70 percent / acetic acid / H2O / 0.17 h / 120 °C View Scheme

1: 1.) NaH / 1.) ether, 0 deg C, 20 min, 2.) ether, RT, 1.5 h 2: 1.) CuI / 1.) ether, 0 deg C, 30 min, 2.) ether, -78 deg C, 3 h 3: 96 percent / diisobutylaluminum hydride / CH2Cl2 / 1 h / -78 °C 4: 94 percent / CBr4, Ph3P / CH2Cl2 / 3 h / -78 - -60 °C 5: 26 percent / KOH / H2O / 0.67 h 6: 70 percent / acetic acid / H2O / 0.17 h / 120 °C View Scheme