1: 1.) lithium diisopropylamide / 1.) THF, below -65 deg C, 20 min, 2.a) THF, below -65 deg C, 1.5 h, b) to -10 deg C 2: 75 percent / potassium hydride / dimethylformamide / 1 h / 0 °C 3: 53 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O / 19 h / 70 °C / other oxidants (without catalyst), solvents temperatures, reaction times 4: 1.) 0.6N aq. HCl, 2.) Jones reagent / 1.) THF, reflux, 3 h, 2.) acetone, 0 deg C, 40 min 5: H2 / 5percent Pd/C / methanol / 1 h 6: concd. HCl / 0.67 h / Heating 7: 2.) N,N'-dicyclohexylcarbodiimide, TEA / 1.) 70 deg C, 7 h, 2.) 55 deg C, 5.5 h 8: H2 / 5percent Pd/C / methanol / 1 h / Ambient temperature 9: 1.) N,N'-carbonyldiimidazole / 1.) DMF, acetonitrile, r.t., 1.5 h, 2.) r.t., overnight 10: 74 percent / p-carboxybenzenesulfonyl azide, TEA / ethyl acetate / 0.5 h / Ambient temperature 11: 74 percent / Rh2(OAc)4 / benzene / 0.05 h / Heating 12: N,N-diisopropylethylamine / acetonitrile / 1.5 h / -20 °C View Scheme