1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 4.5 h / 20 °C 2: toluene / 18 h / Molecular sieve; Reflux 3: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 18 h / 0 - 20 °C 4: pyridine hydrogenfluoride / tetrahydrofuran / 7 h / 0 - 20 °C View Scheme

1.1: i-Pr2NEt / CH2Cl2 / 0.67 h / 0 °C 2.1: NaI / acetone 3.1: LiCl; n-BuLi; i-Pr2NH / tetrahydrofuran; hexane / 1 h / -80 - 0 °C 3.2: 80 percent / tetrahydrofuran; hexane / 0 - 4 °C 4.1: 1 N NaOH / methanol; H2O / 4 h / Heating View Scheme

1: 3.59 g / pyridinium chlorochromate / CH2Cl2 / 5 h / 0 °C 2: 1.99 g / diethyl ether / 1 h / -78 °C 3: 83 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 2 h / -78 - -20 °C 4: 51 percent / HCl; NaBH3CN / methanol / 24 h / 20 °C 5: 83 percent / H2SO4 / methanol / 3.5 h / 20 °C View Scheme

1H-imidazole; bromine; triphenylphosphine in diethyl ether; acetonitrile T=23°C; 18 h;