1.1: (diacetoxyiodo)benzene; KOH / methanol 1.2: 61 percent / Acid hydrolysis 2.1: 75 percent / TMSOTf; Et3N View Scheme

1: H2 / Pd-C / ethanol 2: LDA / tetrahydrofuran View Scheme

trimethylsilyl trifluoromethanesulfonate; triethylamine Elimination;

1: 83 percent / Br2 / CH2Cl2; CHCl3 / 8 h / -78 °C 2: 82 percent / NaBH4 / CH2Cl2; ethanol; H2O / 21 h / Ambient temperature 3: pyridine / CH2Cl2 / 1 h / 130 °C 4: DBU / diethyl ether; tetrahydrofuran / 22 h / Heating 5: LiAlH4 / diethyl ether / 8 h / Ambient temperature 6: 83 percent / pyridinium chlorochromate, anhydr. sodium acetate / CH2Cl2; ethanol / 1.) 1 h, 0 deg C, 2.) RT, 3 h View Scheme

1: 95 percent / H2 / 10percent Pd/C / diethyl ether / 16 h / 25 °C 2: 82 percent / diisobutylaluminium hydride / toluene / 3 h / -78 °C 3: 86 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 48 h / 20 °C View Scheme