aluminium(III) iodide; tetra-(n-butyl)ammonium iodide in benzene T=10°C;

hydrogenchloride in tetrahydrofuran T=25°C; 216 h;

1: 77.1 percent / Et3N, DMAP / CH2Cl2 / 17 h / 25 °C 2: 1) 9-BBN, 2) NaOH, H2O2 / 1) THF, 25 deg C, 19h, 2a) 0 deg C, 30 min, 2b) 25 deg C, 10h 3: 95 percent / CBr4, PPh3, K2CO3 / CH2Cl2 / 0.5 h / 0 °C 5: 80 percent / 5percent HCl / tetrahydrofuran / 216 h / 25 °C View Scheme

1: 96.6 percent / NEt3, DMAP / CH2Cl2 / 1) 0 deg C, 0.5h, 2) 25 deg C, 4h 2: 1) Cp2Zr(H)Cl, 2) NIS / 1) toluene, 30h, 25 deg C, 2) 62h 4: 80 percent / 5percent HCl / tetrahydrofuran / 216 h / 25 °C View Scheme

1: 1) NaH / 1a) THF, 0 deg C, 25 min, 1b) 25 deg C, 30 min, 2) 25 deg C, 12h 2: 1) Me3Al / 1a) toluene, -6 deg C, 10 min, 1b) 25 deg C, 50 min, 2) toluene, 16h, reflux 3: 1) t-BuLi, 2) ICl / 1) ether, pentane, -45 to 40 deg C, 30 min, 2) -78 to 25 deg C 4: 2) Na2CO3 / 1) CH2Cl2, 25 deg C, 7.5h, 2) MeOH, 25 deg C, 12h 5: 1) NaH / 1a) THF, 0 deg C, 30 min, 1b) 25 deg C, 2.5h, 2a) 0 deg C, 1.5h, 2b) 25 deg C, 21.5h 6: 86 percent / LiOH-H2O / tetrahydrofuran; methanol; H2O / 65 h / 75 °C 8: 80 percent / 5percent HCl / tetrahydrofuran / 216 h / 25 °C View Scheme

1: 1) Cp2Zr(H)Cl, 2) NIS / 1) toluene, 30h, 25 deg C, 2) 62h 3: 80 percent / 5percent HCl / tetrahydrofuran / 216 h / 25 °C View Scheme

1: 95 percent / CBr4, PPh3, K2CO3 / CH2Cl2 / 0.5 h / 0 °C 3: 80 percent / 5percent HCl / tetrahydrofuran / 216 h / 25 °C View Scheme

2: 80 percent / 5percent HCl / tetrahydrofuran / 216 h / 25 °C View Scheme

2: 80 percent / 5percent HCl / tetrahydrofuran / 216 h / 25 °C View Scheme

1: 1) NaH / 1a) THF, 0 deg C, 30 min, 1b) 25 deg C, 2.5h, 2a) 0 deg C, 1.5h, 2b) 25 deg C, 21.5h 2: 86 percent / LiOH-H2O / tetrahydrofuran; methanol; H2O / 65 h / 75 °C 4: 80 percent / 5percent HCl / tetrahydrofuran / 216 h / 25 °C View Scheme