sodium formate; N-hexadecyl-N,N,N-trimethylammonium bromide; sodium lauryl sulfate; (R,R)-TsDPEN; [{(η5-C5Me5)RhCl}2(μ-Cl)2] in water T=28°C; 2.5 h;

potassium carbonate in acetone T=100°C; 3 h;

TriEACC in 1,2-dichloro-ethane 2 h;

zinc in methanol; acetic acid 0.0833333 h;

1: 76 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran / 1.) 0 deg C, 45 min, 2.) r.t., 1 h 2: 3 percent / manganese(III) acetate, acetic acid / 22 h / Ambient temperature View Scheme

potassium carbonate Alkylation;

tetra-n-butylammonium tribromide in tetrahydrofuran; methanol T=20°C; 24 h;

hydrogen; palladium on activated charcoal in acetone

1: 1.) Mg, iodine; 2.) 10 percent H2SO4 / 1.) ether, 3-4 h, reflux; 2.) ether 2: p-toluenesulphonic acid, K2CO3 / benzene / Heating 3: H2 / palladium-on-charcoal / methanol 4: 26 percent / BF3*Et2O / benzene / 1.) 5 h; 2.) 16 h 5: 56 percent / SnCl4 / CH2Cl2; H2O / 2 h 6: 28 percent / AlCl3, AlBr3 / CH2Cl2 7: 35 percent / NaBH4 / ethanol / 0.5 h View Scheme