1: (n-propyl)-triphenylphosphonium bromide With sodium hexamethyldisilazane in tetrahydrofuran T=0 - 20°C; Wittig reaction; Inert atmosphere; 2: 15-oxo-pentadecanoic acid methyl ester in tetrahydrofuran T=-78 - 20°C; Wittig reaction; Inert atmosphere; stereoselective reaction;

1: Raney nickel; ethanol / 100 °C / 73550.8 Torr / Hydrogenation 2: ethanol; hydrazine hydrate View Scheme

1: Raney nickel; ethanol / 100 °C / 73550.8 Torr / Hydrogenation 2: alkaline solution View Scheme

1: 28 percent / nBuLi / tetrahydrofuran / 0 °C 2: 99 percent / H2 / 10 percent Pd/C / ethyl acetate / 26 h 3: 88 percent / aq. KOH / ethanol / 17 h / 20 °C View Scheme

sodium tetrahydroborate in methanol T=0°C; 0.25 h;

1: 87 percent / MeONa / dimethylformamide / 24 h / 0 - 5 °C 2: H2 / Pd/C / ethanol / 2585.74 - 10343 Torr 3: 0.56 g / NaOH / H2O View Scheme