anhydrous iron chloride; acetyl chloride in 1,2-dichloro-ethane 72 h;

1: acetic anhydride; 1-(tert-butyldiphenylsiloxy)-2-phenylethane With perchloric acid immobilized on silica gel in dichloromethane T=20°C; 10 h; 2: methanol 0.5 h;

1: methanol With 1H-imidazole in dichloromethane 0.166667 h; Inert atmosphereCooling; 2: tert-butylchlorodiphenylsilane in dichloromethane T=20°C; Inert atmosphere;

4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in dichloromethane T=20°C; Inert atmosphere;

1: 1.) n-BuLi / 1.) THFm HMPA, hexane, -80 deg C -> -30 deg C, 30 min; -30 deg C, 45 min, 2.) room temperature, 30 h 2: 87 percent / CBr4, Ph3P / CH2Cl2 / 0.75 h 3: 2.) CuCl / 1.) THF, room temperature, 2.5 h, 2.) 40 deg C, 3 h 4: 96 percent / Ni(OAc)4*4H2O, NaBH4, H2, ethylenediamine / aq. ethanol / 4 h 5: 69 percent / CBr4, Ph3P / CH2Cl2 / 0 °C 6: 380 mg / 12M HCl / methanol; tetrahydrofuran / 24 h / 0 °C View Scheme

1: 96 percent / Ni(OAc)4*4H2O, NaBH4, H2, ethylenediamine / aq. ethanol / 4 h 2: 69 percent / CBr4, Ph3P / CH2Cl2 / 0 °C 3: 380 mg / 12M HCl / methanol; tetrahydrofuran / 24 h / 0 °C View Scheme

1: I2 / 60 °C 2: 60 °C View Scheme

1: 1.) Na / 1.) THF, 3 h, reflux, 2.) 20 h, reflux 2: I2 / 60 °C 3: 60 °C View Scheme

T=60°C; Yield given;

sulfuric acid Inert atmosphereReflux;