tetrakis(triphenylphosphine) palladium(0); n-butyllithium 1.) THF, hexane, -78 deg C, 2.) THF, hexane, a) -78 deg C, 1 h, b) RT, overnight; Yield given. Multistep reaction;

1: HBr / petroleum ether / 0.33 h / 20 °C / Irradiation 2: 40percent CH3CO3H, BF3*Et2O / CHCl3 / 120 h / 50 °C 3: 15 percent Chromat. / 1) Br(CH2)2Br, Li (with 1percent Na), 2) 85percent H3PO4 / tetrahydrofuran / 0.17 h / 66 °C / 1) THF, 66 deg C, 10 min, 2) toluene, reflux, 2 h 4: 91 percent / H2 / 10percent Pd/C / ethanol View Scheme

2: 72 percent / dibenzo-18-crown-6 / dioxane / 7 h / Heating 3: 90 percent / KOH / ethanol / 0.5 h / 50 °C View Scheme

2: 72 percent / dibenzo-18-crown-6 / dioxane / 7 h / Heating 3: p-TsOH / ethanol View Scheme

potassium permanganate; sulfuric acid; N-benzyl-N,N,N-triethylammonium chloride; acetic acid in dichloromethane; water T=20°C; 2 h;

peracetic acid; sodium hydroxide; sodium hydrogen sulphate in petrol ether; water; ethyl acetate; thiophenol

meta-chloroperoxybenzoic acid; hydrogen bromide in hexane T=20°C; 3 h;

1: AIBN / 10 h / 80 °C 2: 40percent CH3CO3H / 1,1,1-trichloro-ethane / 30 °C View Scheme