1: (COCl)2; DMSO; Et3N 2: NaH / tetrahydrofuran / 0 - 20 °C View Scheme

AlCl3, aluminium chloride in dichloromethane T=0°C; chemoselective reaction;

AlCl3, aluminium chloride in toluene T=0°C; chemoselective reaction;

acide phosphorique T=180 - 200°C;

oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-60 - -50°C; 0.5 h;

1: 1.) DMSO; 2.) oxalyl chloride, triethylamine / 1.) CH2Cl2, -50 deg C, 5 min; 2.) CH2Cl2, -50 deg C 20 min, rt 2: potassium t-butoxide / 1.) THF-HMPA, -60 deg C, 30 min; 2.) -20 deg C 5 min, rt overnight 3: 95 percent / p-toluenesulfonic acid / methanol / 2 h / Ambient temperature 4: hydrogen / Pt-C / ethyl acetate 5: 1.) DMSO; 2.) oxalyl chloride, triethylamine / 1.) CH2Cl2, -78 deg C, 5 min; 2.) CH2Cl, -78 deg C 5 min, rt 6: 1.) n-butyllithium / 1.) THF-hexane, 0 deg C 30 min; 2.) THF-hexane, -30 deg C 40 min, rt 7: 97 percent / NaOH / dimethylsulfoxide / 24 h / Heating 8: 67 percent / NaH, ethanethiol / dimethylformamide / 1.) 0 deg C, 30 min rt; 2.) reflux 3 h View Scheme

1: With sodium periodate in methanol; water T=45°C; 2 h; 2: With water; sodium carbonate in methanol T=20°C; 2 h;

Rh(acetylacetonate)(CO)2; 6-[bis(4-fluorophenyl)phosphanyl]-1H-pyridin-2-one; N-(5-bis(4-methoxyphenyl)phosphanylpyrrol-2-carbonyl)guanidine; hydrogen in toluene T=80°C; P=15001.5 Torr; 24 h; Inert atmosphereAutoclave; regioselective reaction;

tin(ll) chloride in chloroform 24 h;

lithium aluminium tetrahydride in diethyl ether a. reflux while adding reagent b. overnight room temperature c. reflux, 3h;