1: copper dichloride; triethyl amine hydrochloride / acetonitrile / 8 h / 80 °C 2: anhydrous iron chloride / dichloromethane / 24 h / 40 °C 3: potassium tert-butylate / tetrahydrofuran / 1.5 h / -20 °C 4: Pd(1,2-bis(diphenylphosphino)ethane)Cl2; lithium triethylborohydride / tetrahydrofuran / 2 h / 20 °C 5: ammonium cerium (IV) nitrate; nitric acid / water; acetonitrile; tetrahydrofuran / 0.5 h / 0 °C View Scheme

1: (all-E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl bromide With tri-n-butyl-tin hydride; lithium diisopropyl amide in tetrahydrofuran; hexane 2 h; 2: 2,3-Dimethoxy-5-methyl-1,4-benzoquinone With silver(l) oxide; boron trifluoride diethyl etherate in dichloromethane 2 h; Further stages.;

1.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C 1.2: ZnBr2 / tetrahydrofuran; diethyl ether / -78 - 0 °C 1.3: 90 percent / Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 2.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C 2.2: ZnBr2 / tetrahydrofuran; diethyl ether / -78 - 0 °C 2.3: 79 percent / Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; pentane; diethyl ether / 23 °C 3.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C 3.2: ZnBr2 / tetrahydrofuran; diethyl ether / -78 - 0 °C 3.3: 83 percent / Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 4.1: 81 percent / KOH; H2O / methanol / 2 h / Heating 5.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 8 h / 23 °C 5.2: 88 percent / I2 / tetrahydrofuran; 1,2-dichloro-ethane / 0.25 h / 0 °C 6.1: t-BuLi / diethyl ether; pentane / -78 °C 6.2: ZnBr2 / diethyl ether; tetrahydrofuran / -78 - 0 °C 6.3: Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 7.1: 84 percent / KOH / methanol; H2O / Heating 8.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 1 h / 23 °C 8.2: 90 percent / Cl2Ni(PPh)2; n-BuLi; PPh3 / tetrahydrofuran / 1 h / 23 °C View Scheme

1.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C 1.2: ZnBr2 / tetrahydrofuran; diethyl ether / -78 - 0 °C 1.3: 79 percent / Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; pentane; diethyl ether / 23 °C 2.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C 2.2: ZnBr2 / tetrahydrofuran; diethyl ether / -78 - 0 °C 2.3: 83 percent / Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 3.1: 81 percent / KOH; H2O / methanol / 2 h / Heating 4.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 8 h / 23 °C 4.2: 88 percent / I2 / tetrahydrofuran; 1,2-dichloro-ethane / 0.25 h / 0 °C 5.1: t-BuLi / diethyl ether; pentane / -78 °C 5.2: ZnBr2 / diethyl ether; tetrahydrofuran / -78 - 0 °C 5.3: Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 6.1: 84 percent / KOH / methanol; H2O / Heating 7.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 1 h / 23 °C 7.2: 90 percent / Cl2Ni(PPh)2; n-BuLi; PPh3 / tetrahydrofuran / 1 h / 23 °C View Scheme

1.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C 1.2: ZnBr2 / tetrahydrofuran; diethyl ether / -78 - 0 °C 1.3: 83 percent / Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 2.1: 81 percent / KOH; H2O / methanol / 2 h / Heating 3.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 8 h / 23 °C 3.2: 88 percent / I2 / tetrahydrofuran; 1,2-dichloro-ethane / 0.25 h / 0 °C 4.1: t-BuLi / diethyl ether; pentane / -78 °C 4.2: ZnBr2 / diethyl ether; tetrahydrofuran / -78 - 0 °C 4.3: Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 5.1: 84 percent / KOH / methanol; H2O / Heating 6.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 1 h / 23 °C 6.2: 90 percent / Cl2Ni(PPh)2; n-BuLi; PPh3 / tetrahydrofuran / 1 h / 23 °C View Scheme

4: 77 percent / CuCl / tetrahydrofuran / -50 °C 5: 89 percent / BuLi, p-Me-C6H4-SO2Cl, LiBr 7: Na, EtOH / tetrahydrofuran / Ambient temperature 8: 1.) H(+), 2.) air View Scheme

1.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 8 h / 23 °C 1.2: 88 percent / I2 / tetrahydrofuran; 1,2-dichloro-ethane / 0.25 h / 0 °C 2.1: t-BuLi / diethyl ether; pentane / -78 °C 2.2: ZnBr2 / diethyl ether; tetrahydrofuran / -78 - 0 °C 2.3: Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 3.1: 84 percent / KOH / methanol; H2O / Heating 4.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 1 h / 23 °C 4.2: 90 percent / Cl2Ni(PPh)2; n-BuLi; PPh3 / tetrahydrofuran / 1 h / 23 °C View Scheme

1.1: 81 percent / KOH; H2O / methanol / 2 h / Heating 2.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 8 h / 23 °C 2.2: 88 percent / I2 / tetrahydrofuran; 1,2-dichloro-ethane / 0.25 h / 0 °C 3.1: t-BuLi / diethyl ether; pentane / -78 °C 3.2: ZnBr2 / diethyl ether; tetrahydrofuran / -78 - 0 °C 3.3: Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 4.1: 84 percent / KOH / methanol; H2O / Heating 5.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 1 h / 23 °C 5.2: 90 percent / Cl2Ni(PPh)2; n-BuLi; PPh3 / tetrahydrofuran / 1 h / 23 °C View Scheme

1.1: t-BuLi / diethyl ether; pentane / -78 °C 1.2: ZnBr2 / diethyl ether; tetrahydrofuran / -78 - 0 °C 1.3: Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 2.1: 84 percent / KOH / methanol; H2O / Heating 3.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 1 h / 23 °C 3.2: 90 percent / Cl2Ni(PPh)2; n-BuLi; PPh3 / tetrahydrofuran / 1 h / 23 °C View Scheme

1.1: 84 percent / KOH / methanol; H2O / Heating 2.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 1 h / 23 °C 2.2: 90 percent / Cl2Ni(PPh)2; n-BuLi; PPh3 / tetrahydrofuran / 1 h / 23 °C View Scheme