tetrabutyl ammonium fluoride; triethylamine in tetrahydrofuran T=21°C; 25 h;

1: 1.) n-BuLi / 1.) THF, HMPA, -78 deg C 2: 41 percent / Br2 / CH2Cl2 / -78 °C 4: 72 percent / (NH4)2SO4, tert-butyl alcohol, NH3, Li / tetrahydrofuran 5: 88 percent / Et3N, 1M tetra-n-butylammonium fluoride / tetrahydrofuran / 25 h / 21 °C View Scheme

2: 72 percent / (NH4)2SO4, tert-butyl alcohol, NH3, Li / tetrahydrofuran 3: 88 percent / Et3N, 1M tetra-n-butylammonium fluoride / tetrahydrofuran / 25 h / 21 °C View Scheme

1: 41 percent / Br2 / CH2Cl2 / -78 °C 3: 72 percent / (NH4)2SO4, tert-butyl alcohol, NH3, Li / tetrahydrofuran 4: 88 percent / Et3N, 1M tetra-n-butylammonium fluoride / tetrahydrofuran / 25 h / 21 °C View Scheme

1: 90 percent / TEA, DMAP / tetrahydrofuran; dimethylformamide / 24 h / Heating 2: 1.) Cp2ZrCl2, 2.) iodine / 1.) CH2Cl2, toluene, 21 deg C, 6 h, 2.) CH2Cl2, toluene, THF, 0 deg C, 20 min. 4: 72 percent / (NH4)2SO4, tert-butyl alcohol, NH3, Li / tetrahydrofuran 5: 88 percent / Et3N, 1M tetra-n-butylammonium fluoride / tetrahydrofuran / 25 h / 21 °C View Scheme

1: 1.) Cp2ZrCl2, 2.) iodine / 1.) CH2Cl2, toluene, 21 deg C, 6 h, 2.) CH2Cl2, toluene, THF, 0 deg C, 20 min. 3: 72 percent / (NH4)2SO4, tert-butyl alcohol, NH3, Li / tetrahydrofuran 4: 88 percent / Et3N, 1M tetra-n-butylammonium fluoride / tetrahydrofuran / 25 h / 21 °C View Scheme

2: 72 percent / (NH4)2SO4, tert-butyl alcohol, NH3, Li / tetrahydrofuran 3: 88 percent / Et3N, 1M tetra-n-butylammonium fluoride / tetrahydrofuran / 25 h / 21 °C View Scheme

1: 72 percent / (NH4)2SO4, tert-butyl alcohol, NH3, Li / tetrahydrofuran 2: 88 percent / Et3N, 1M tetra-n-butylammonium fluoride / tetrahydrofuran / 25 h / 21 °C View Scheme

N-iodo-succinimide in dichloromethane T=0 - 20°C; 3 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;