1: Bu4NOAc; Pd(IiPr)(OAc)2*(H2O); O2 / toluene / 12 h / 60 °C 2: 38 mg / PPh3; RhCl(PPh3)3 / toluene; dioxane; propan-2-ol / 50 °C View Scheme

2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; [bis(acetoxy)iodo]benzene in dichloromethane T=20°C; 5 h; Inert atmosphere;

1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / |Inert atmosphere 2: diethyl ether / 0 °C / |Inert atmosphere 3: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / |Inert atmosphere 4: tetrabutyl ammonium fluoride / tetrahydrofuran / |Inert atmosphere View Scheme

1: Dess-Martin periodinane / CH2Cl2 / 20 °C 2: NaH / tetrahydrofuran 3: NaOH View Scheme

1: PCC/silica / CH2Cl2 / 0.83 h / ultrasound 2: MgSO4 / diethyl ether / 1 h / Ambient temperature 4: 89 percent / Li / tetrahydrofuran; liquid ammonia / 1 h / Heating 5: 1) n-BuLi / 1) THF/hexane, -78 deg C, 10 h, 2) THF, -78 deg C to rt, 12 h 6: N2H4 / methanol / 4 h / Heating 7: 99 percent / nBu4NF / tetrahydrofuran / Ambient temperature 8: NEt3 / CH2Cl2 / 0.25 h / 0 °C 9: KOtBu / tetrahydrofuran / 1) 0 deg C, 10 min, 2) rt, 30 min 10: 79 percent / anisole, trifluoroacetic acid / CH2Cl2 / 0.25 h View Scheme