1.1: 61 percent / AD-mix-α; methanesulfonamide; sodium hydrogen carbonate / 2-methyl-propan-2-ol; H2O / 25 h / 0 °C 2.1: 92 percent / thionyl chloride / CCl4 / 22 h / Heating 3.1: copper(I) cyanide / tetrahydrofuran; hexane / 0.25 h / 20 °C 3.2: 84 percent / boron trifluoride diethyl etherate / tetrahydrofuran; hexane / 1 h / -78 °C 4.1: 74 percent / acetic acid; zinc / 4 h / 20 °C 5.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C 5.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C 6.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C 7.1: hydrogen / Pd/C / tetrahydrofuran / 3 h / 20 °C 8.1: 6.5 mg / diethyl ether / 0.33 h / 20 °C View Scheme

1: (2E,4E)-hexadecadienoic acid With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane T=0 - 25°C; 1 h; 2: 2,2,2-trichloroethyl alcohol With 4-(N,N-dimethlyamino)pyridine; triethylamine T=20°C; 20 h;

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=20°C; 20 h;

1: 86 percent / potassium hydroxide / tetrahydrofuran; H2O / 22 h / Heating 2: oxalyl chloride; dimethylformamide / CH2Cl2 / 0.83 h / 20 °C 3: 4.41 g / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / 20 °C View Scheme

1: 68 percent / molecular sieves 4 Angstroem; lithium hydroxide / tetrahydrofuran / 40 h / Heating 2: 86 percent / potassium hydroxide / tetrahydrofuran; H2O / 22 h / Heating 3: oxalyl chloride; dimethylformamide / CH2Cl2 / 0.83 h / 20 °C 4: 4.41 g / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / 20 °C View Scheme

1: oxalyl chloride; dimethylformamide / CH2Cl2 / 0.83 h / 20 °C 2: 4.41 g / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 20 h / 20 °C View Scheme

1.1: 61 percent / AD-mix-α; methanesulfonamide; sodium hydrogen carbonate / 2-methyl-propan-2-ol; H2O / 25 h / 0 °C 2.1: 92 percent / thionyl chloride / CCl4 / 22 h / Heating 3.1: copper(I) cyanide / tetrahydrofuran; hexane / 0.25 h / 20 °C 3.2: 84 percent / boron trifluoride diethyl etherate / tetrahydrofuran; hexane / 1 h / -78 °C 4.1: 74 percent / acetic acid; zinc / 4 h / 20 °C 5.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C 5.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C 6.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C View Scheme