titanium tetrachloride; zinc in tetrahydrofuran; dichloromethane T=0°C; 4 h; Yield given;

1.1: triphenylphosphine / dichloromethane / 0 °C / Inert atmosphere 1.2: 4 h / 0 °C / Inert atmosphere 2.1: lanthanum; iodine / tetrahydrofuran / 3 h / 67 °C / Inert atmosphere View Scheme

lt;Yb(H2O)9gt;(OTf)3 in ethanol 48 h; Heating;

1.1: 68 percent / molecular sieves 4 Angstroem; lithium hydroxide / tetrahydrofuran / 40 h / Heating 2.1: 86 percent / potassium hydroxide / tetrahydrofuran; H2O / 22 h / Heating 3.1: oxalyl chloride; dimethylformamide / CH2Cl2 / 0.83 h / 20 °C 4.1: 4.41 g / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / 20 °C 5.1: 61 percent / AD-mix-α; methanesulfonamide; sodium hydrogen carbonate / 2-methyl-propan-2-ol; H2O / 25 h / 0 °C 6.1: 92 percent / thionyl chloride / CCl4 / 22 h / Heating 7.1: copper(I) cyanide / tetrahydrofuran; hexane / 0.25 h / 20 °C 7.2: 84 percent / boron trifluoride diethyl etherate / tetrahydrofuran; hexane / 1 h / -78 °C 8.1: 74 percent / acetic acid; zinc / 4 h / 20 °C 9.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C 9.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C 10.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C View Scheme

1: With acetic acid in acetonitrile 0.166667 h; 2: With ammonium acetate in acetonitrile T=80°C; 8 h;

diethyl ether Leiten des Reaktionsprodukts ueber Aluminiumoxid bei 280grad und Hydrieren des erhaltenen Oleefin-Gemisches an Raney-Nickel bei 150grad/100 at;

chromium dichloride in tetrahydrofuran T=25°C; 5 h;

1: With boron trifluoride diethyl etherate in dichloromethane T=25°C; 1 h; 2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane T=25°C; 1 h; Further byproducts given;

1: With boron trifluoride diethyl etherate in dichloromethane T=25°C; 1 h; 2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane T=25°C; 1 h; Further byproducts given;

1.1: Br2 / dioxane; CH2Cl2; diethyl ether 2.1: Mg / diethyl ether 2.2: diethyl ether 3.1: NaI / dimethylformamide; acetone / 20 h / Heating 4.1: monoperoxyphthalic acid / CH2Cl2 / 0 - 5 °C View Scheme