1: With sodium bis(2-methoxyethoxy)aluminium dihydride in diethyl ether; toluene T=0 - 20°C; Corey reductive iodination; 2: With iodine in diethyl ether; ethyl acetate; toluene T=-78 - 20°C; Corey reductive iodination; 2 h; Further stages.;

1: With sodium bis(2-methoxyethoxy)aluminium dihydride in tetrahydrofuran; toluene T=0°C; 72 h; 2: With ethyl acetate in tetrahydrofuran; toluene T=0°C; 0.00555556 h; 3: With iodine in tetrahydrofuran; toluene T=-78°C; 2 h; Further stages.;

1.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 1 h / -30 °C 1.2: 90 percent / tetrahydrofuran; hexane / 2 h / -30 °C 2.1: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene / 72 h / 0 °C 2.2: EtOAc / toluene; tetrahydrofuran / 0.01 h / 0 °C 2.3: 72 percent / I2 / toluene; tetrahydrofuran / 2 h / -78 °C View Scheme

iodine in tetrahydrofuran T=-78 - 20°C; 1 h;

1: 1.) n-BuLi, 2.) DIBAL, 3.) I2 / 1.) Et2O-hexane, -20 deg C, 2.) 35 deg C, 48 h, 3.) -78 deg C 2: 1.) n-BuLi, 2.) DIBAL, 3.) I2 / 1.) Et2O-hexane, -20 deg C, 2.) 35 deg C, 48 h, 3.) -78 deg C View Scheme

n-butyllithium; iodine; diisobutylaluminium hydride 1.) Et2O-hexane, -20 deg C, 2.) 35 deg C, 48 h, 3.) -78 deg C; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

n-butyllithium; iodine; diisobutylaluminium hydride 1.) Et2O-hexane, -20 deg C, 2.) 35 deg C, 48 h, 3.) -78 deg C; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

(i) CuI, (ii) I2; Multistep reaction;