Dess-Martin periodane in dichloromethane T=20°C; Oxidation; 1 h;

1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 1.2: tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: TiCl4 / CH2Cl2 / 0.17 h / -78 °C 3.1: HMDS / CH2Cl2 / 4 h / -78 - 20 °C 4.1: MCPBA / hexane / 4 h / 20 °C 4.2: 0.4 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 5.1: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C View Scheme

1.1: HMDS / CH2Cl2 / 4 h / -78 - 20 °C 2.1: MCPBA / hexane / 4 h / 20 °C 2.2: 0.4 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 3.1: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C View Scheme

1.1: MCPBA / hexane / 4 h / 20 °C 1.2: 0.4 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 2.1: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C View Scheme

1.1: TiCl4 / CH2Cl2 / 0.17 h / -78 °C 2.1: HMDS / CH2Cl2 / 4 h / -78 - 20 °C 3.1: MCPBA / hexane / 4 h / 20 °C 3.2: 0.4 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 4.1: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C View Scheme

1: With PHT in tetrahydrofuran T=20°C; Bromination; 1 h; 2: With lithium carbonate; lithium bromide in N,N-dimethyl-formamide Aromatisation; 2 h; Heating;