1: 92 percent / piperidine, glacial acetic acid / CHCl3 / 14 h / Heating 2: 90 percent / sodium borohydride / ethanol / 0.67 h / 15 - 20 °C 3: 55 percent / Cu, pyridine / methanol / 36 h / Heating 4: 88 percent / lithium aluminium hydride / diethyl ether / Heating 5: 92 percent / pydidinum chlorochromate, celite, sodium acetate / CH2Cl2 / 5 h View Scheme

water; oxygen T=20°C; 24 h;

1: 16 percent / lithium / tetrahydrofuran / 1 h / sonication 2: 90 percent / PCC; silica gel / CH2Cl2 / 3 h / 20 °C 3: 90 percent / tetrahydrofuran / 2 h / sonication 4: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 5: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 6: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 7: 28 percent / propionic acid / 48 h / 180 °C 8: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 9: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 10: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 11: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 12: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme

1: With potassium tert-butylate in tetrahydrofuran T=20°C; 2 h; 2: With sulfuric acid in tetrahydrofuran T=20°C; Further stages.;

1: (methoxymethyl)-triphenylphosphonium chloride With potassium tert-butylate in tetrahydrofuran T=0°C; 1 h; Inert atmosphere; 2: 2,2-dimethylpent-4-enal in tetrahydrofuran T=0 - 20°C; 2.5 h; 3: With sulfuric acid in tetrahydrofuran; water T=0 - 20°C; Inert atmosphere;