1: (5Z,9E,11Z)-1-bromo-heptadeca-5,9,11-triene With lithium in diethyl ether T=0°C; 2 h; 2: carbon dioxide in diethyl ether T=-20°C; 2 h;

1.1: 80 percent / piperidine; Pd(PPh3)4; CuI / tetrahydrofuran / 5 h / 20 °C 2.1: 81 percent / Fe(acac)3 / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 1 h / 0 °C 3.1: aq. HCl / tetrahydrofuran / 1.5 h / 70 °C 4.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -78 °C 4.2: 3.16 g / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2.5 h / -78 - 20 °C 5.1: disiamylborane / tetrahydrofuran / 4.25 h / -20 - 0 °C 5.2: 76 percent / glacial acetic acid / tetrahydrofuran / 20 °C 6.1: 90 percent / triphenylphosphine dibromide / CH2Cl2 / 1.5 h / 20 °C 7.1: Li / diethyl ether / 2 h / 0 °C 7.2: 34 percent / diethyl ether / 2 h / -20 °C View Scheme

1.1: 81 percent / Fe(acac)3 / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 1 h / 0 °C 2.1: aq. HCl / tetrahydrofuran / 1.5 h / 70 °C 3.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -78 °C 3.2: 3.16 g / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2.5 h / -78 - 20 °C 4.1: disiamylborane / tetrahydrofuran / 4.25 h / -20 - 0 °C 4.2: 76 percent / glacial acetic acid / tetrahydrofuran / 20 °C 5.1: 90 percent / triphenylphosphine dibromide / CH2Cl2 / 1.5 h / 20 °C 6.1: Li / diethyl ether / 2 h / 0 °C 6.2: 34 percent / diethyl ether / 2 h / -20 °C View Scheme