1: triphenyl-methyl-phosphonium iodide With n-butyllithium in tetrahydrofuran; hexane T=20°C; 1 h; 2: 8-acetoxy-6-methyloctan-2-one in tetrahydrofuran; hexane T=0 - 20°C;

1.1: NaH / benzene; dimethylformamide / 3 h / 20 °C 1.2: 96 percent / benzene; dimethylformamide / 12 h / Heating 2.1: 81 percent / LiI / dimethylformamide / 12 h / Heating 3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 3.2: 85 percent / tetrahydrofuran; hexane / 0 - 20 °C View Scheme

1.1: 81 percent / LiI / dimethylformamide / 12 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C 2.2: 85 percent / tetrahydrofuran; hexane / 0 - 20 °C View Scheme

1.1: Hg(OAc)2 / 25 h / 5 - 20 °C 1.2: 97 percent / NaOH; NaBH4 / H2O / 3 h / 0 - 20 °C 2.1: 90 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 20 °C View Scheme

potassium hydroxide in methanol 4 h; Heating;

1: 90 percent / KOH / methanol / 4 h / Heating 2: H2 / Pd/C / methanol / 5 h View Scheme

potassium hydroxide in methanol 4 h; Heating;