1: 73 percent / TPAP, NMO, 4 Angstroem sieves / CH2Cl2 / 3 h 2: 85 percent / tetrahydrofuran; hexane / 2 h / 0 - 20 °C View Scheme

1: 79 percent / tetrahydrofuran / 12 h / Ambient temperature 2: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 3: 73 percent / TPAP, NMO, 4 Angstroem sieves / CH2Cl2 / 3 h 4: 85 percent / tetrahydrofuran; hexane / 2 h / 0 - 20 °C View Scheme

1: 86 percent / LiCl, MsCl, s-collidine / dimethylformamide / 2 h / 0 - 20 °C 2: 79 percent / tetrahydrofuran / 12 h / Ambient temperature 3: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 4: 73 percent / TPAP, NMO, 4 Angstroem sieves / CH2Cl2 / 3 h 5: 85 percent / tetrahydrofuran; hexane / 2 h / 0 - 20 °C View Scheme

1: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 2: 73 percent / TPAP, NMO, 4 Angstroem sieves / CH2Cl2 / 3 h 3: 85 percent / tetrahydrofuran; hexane / 2 h / 0 - 20 °C View Scheme

1: 78 percent / LiBH4 / tetrahydrofuran / 0.5 h / 20 °C 2: 86 percent / LiCl, MsCl, s-collidine / dimethylformamide / 2 h / 0 - 20 °C 3: 79 percent / tetrahydrofuran / 12 h / Ambient temperature 4: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 5: 73 percent / TPAP, NMO, 4 Angstroem sieves / CH2Cl2 / 3 h 6: 85 percent / tetrahydrofuran; hexane / 2 h / 0 - 20 °C View Scheme

1: Methyltriphenylphosphonium bromide With sodium amide in tetrahydrofuran 1 h; Heating; 2: (2E,4Z)-2,4-heptadienal in tetrahydrofuran T=-10 - 0°C; Wittig reaction; 1 h; Further stages.;

1: (n-propyl)-triphenylphosphonium bromide With sodium amide in tetrahydrofuran 1 h; Heating; 2: trans-2,4-pentadienal in tetrahydrofuran T=-10 - 0°C; Wittig reaction; 1 h; Further stages. Title compound not separated from byproducts.;

1: 15 percent / LiAlH4 / tetrahydrofuran / 48 h / Heating 2: 1.) NaH / 1.) THF, 30 min, 2.) THF, 2 h 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 2 h, 2.) 2.) CH2Cl2, from -78 deg C to RT, 75 min 4: 78 percent / LiBH4 / tetrahydrofuran / 0.5 h / 20 °C 5: 86 percent / LiCl, MsCl, s-collidine / dimethylformamide / 2 h / 0 - 20 °C 6: 79 percent / tetrahydrofuran / 12 h / Ambient temperature 7: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 8: 73 percent / TPAP, NMO, 4 Angstroem sieves / CH2Cl2 / 3 h 9: 85 percent / tetrahydrofuran; hexane / 2 h / 0 - 20 °C View Scheme

1: aq. NaOH, <PhCH2NEt3>Cl 2: NaOMe / methanol 3: KOtBu 4: MeLi 5: 270 °C View Scheme

1: 33 percent / tetrahydrofuran / 1 h / 0 °C 2: Zn(Cu,Ag) / H2O; methanol / Ambient temperature View Scheme