1: trimethylaluminum; 6,10,14-trimethyl-3E,5E,7E,9E,13-pentadecapentaen-1-yne With zirconocene dichloride in dichloromethane T=23°C; 4 h; 2: T=50°C; 3: 1-((E,E,E,E,E)-3,7-dimethyl-10-bromo-1,3,5,7,9-decapentaenyl)-2,6,6-trimethyl-1-cyclohexene With tris(dibenzylideneacetone)dipalladium (0); zinc(II) chloride in tetrahydrofuran; N,N-dimethyl-formamide T=23°C; 6 h; Further stages.;

1.1: 69 percent 2.1: Cp2ZrCl2 / 1,2-dichloro-ethane / 12 h / 20 °C 2.2: 53 percent / TFP; ZnCl2 / Pd2(dba)3 / tetrahydrofuran; dimethylformamide / 5 h / 20 °C View Scheme

sodium methylate in methanol; N,N-dimethyl-formamide 3 h; Ambient temperature;

1: 40 percent / KOH / tetrahydrofuran / 2 h / Ambient temperature 2: 76 percent / NaBH4 / diethyl ether; methanol / 0.25 h 3: PBr3 / diethyl ether / 2 h / 1.) Et2O, 0 deg C; 2.) room temperature, 2 h 4: 2 h / 60 °C 5: 40 percent / KOH / tetrahydrofuran / 1 h / Ambient temperature 6: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 7: 43 percent / KOH / tetrahydrofuran / 1 h / 0 °C 8: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 9: 2 percent / NaOMe / methanol; dimethylformamide / 3 h / Ambient temperature View Scheme

1: 43 percent / KOH / tetrahydrofuran / 1 h / 0 °C 2: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 3: 2 percent / NaOMe / methanol; dimethylformamide / 3 h / Ambient temperature View Scheme

1: 40 percent / KOH / tetrahydrofuran / 2 h / Ambient temperature 2: 76 percent / NaBH4 / diethyl ether; methanol / 0.25 h 3: PBr3 / diethyl ether / 2 h / 1.) Et2O, 0 deg C; 2.) room temperature, 2 h 4: 2 h / 60 °C 5: 40 percent / KOH / tetrahydrofuran / 1 h / Ambient temperature 6: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 7: 43 percent / KOH / tetrahydrofuran / 1 h / 0 °C 8: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 9: 2 percent / NaOMe / methanol; dimethylformamide / 3 h / Ambient temperature View Scheme

1: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 2: 43 percent / KOH / tetrahydrofuran / 1 h / 0 °C 3: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 4: 2 percent / NaOMe / methanol; dimethylformamide / 3 h / Ambient temperature View Scheme

1: 2 h / 60 °C 2: 40 percent / KOH / tetrahydrofuran / 1 h / Ambient temperature 3: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 4: 43 percent / KOH / tetrahydrofuran / 1 h / 0 °C 5: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 6: 2 percent / NaOMe / methanol; dimethylformamide / 3 h / Ambient temperature View Scheme

1: PBr3 / diethyl ether / 2 h / 1.) Et2O, 0 deg C; 2.) room temperature, 2 h 2: 2 h / 60 °C 3: 40 percent / KOH / tetrahydrofuran / 1 h / Ambient temperature 4: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 5: 43 percent / KOH / tetrahydrofuran / 1 h / 0 °C 6: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 7: 2 percent / NaOMe / methanol; dimethylformamide / 3 h / Ambient temperature View Scheme

1: 76 percent / NaBH4 / diethyl ether; methanol / 0.25 h 2: PBr3 / diethyl ether / 2 h / 1.) Et2O, 0 deg C; 2.) room temperature, 2 h 3: 2 h / 60 °C 4: 40 percent / KOH / tetrahydrofuran / 1 h / Ambient temperature 5: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 6: 43 percent / KOH / tetrahydrofuran / 1 h / 0 °C 7: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 8: 2 percent / NaOMe / methanol; dimethylformamide / 3 h / Ambient temperature View Scheme