1: 53 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O / 19 h / 70 °C / other oxidants (without catalyst), solvents temperatures, reaction times 2: 1.) 0.6N aq. HCl, 2.) Jones reagent / 1.) THF, reflux, 3 h, 2.) acetone, 0 deg C, 40 min 3: H2 / 5percent Pd/C / methanol / 1 h 4: concd. HCl / 0.67 h / Heating 5: 2.) N,N'-dicyclohexylcarbodiimide, TEA / 1.) 70 deg C, 7 h, 2.) 55 deg C, 5.5 h 6: H2 / 5percent Pd/C / methanol / 1 h / Ambient temperature 7: 1.) N,N'-carbonyldiimidazole / 1.) DMF, acetonitrile, r.t., 1.5 h, 2.) r.t., overnight 8: 74 percent / p-carboxybenzenesulfonyl azide, TEA / ethyl acetate / 0.5 h / Ambient temperature 9: 74 percent / Rh2(OAc)4 / benzene / 0.05 h / Heating 10: N,N-diisopropylethylamine / acetonitrile / 1.5 h / -20 °C View Scheme