toluene-4-sulfonamide T=40°C; 48 h;

thionyl chloride T=25 - 27°C; Esterification; 19 h;

30 h; Reflux; regioselective reaction;

1: C32H12BF24(1-)*C54H71IrNP(1+); hydrogen; caesium carbonate / methanol / 4 h / 45 °C 2: potassium carbonate View Scheme

hydrogen; triethylamine; Ru2Cl4((R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2 in tetrahydrofuran; toluene T=35°C; P=2206.5 Torr; 24 h; op = 60percent, var. cat. RuHCl*2<(+)-BINAP>; Title compound not separated from byproducts;

catASium®; hydrogen in dichloromethane P=3000.3 Torr; 48 h; AutoclaveInert atmosphere; enantioselective reaction;

formic acid; (bppm)Rh(1,1,1,5,5,5,-hexafluoroacetylacetonate); triethylamine in dimethylsulfoxide-d6 T=30°C; 8 h;

1: hydrogen / [Rh(COD)(chiral phosphite ligand)2]BF4 / CH2Cl2 / 12 h / 20 °C / 825.07 Torr 2: 98 percent / BH3*SMe2 / tetrahydrofuran / -30 - 0 °C View Scheme

1: 96 percent / SOCl2 / diethyl ether / 0.25 h / Heating 2: 94 percent / Et3N / benzene / 2 h 3: 84 percent / LiCl; NaBH4 / tetrahydrofuran; ethanol / 16 h / 20 °C 4: 70 percent / PPh3; DEAD; diphenylphosphoryl azide / tetrahydrofuran / 24 h / 20 °C 5: tristrimethylsilane; AIBN / benzene / 5 h / Heating 6: 73.6 mg / NaCNBH3 / acetonitrile / 0.25 h / 20 °C 7: 83 percent / NH3; Na / tetrahydrofuran / 0.2 h / -50 °C View Scheme

1: H2 / Pd/C / methanol / 4 h / 20 °C 2: (COCl)2; DMF / tetrahydrofuran / 1 h / 0 - 20 °C View Scheme