1: 1.) 9-BBN, 2.) 30percent aq. H2O2, NaOH / 1.) THF, RT, 26 h, 2.) THF, 50 deg C, 1 h 2: 95 percent / HCl / 19 h View Scheme

sodium periodate; RuO2/BaTi4O9 in phosphate buffer; ethyl acetate T=20°C; pH=6.88; 29 h;

hydrogenchloride; water T=20°C; 15 h;

1: hydrogenchloride; water / 15 h / 20 °C 2: boron trifluoride diethyl etherate / chlorobenzene / 6 h / Reflux View Scheme

sodium periodate; RuO2/BaTi4O9 in phosphate buffer; ethyl acetate T=20°C; pH=6.88; 29 h;

1: acetyl chloride / methanol / 2 h / 0 - 20 °C / Inert atmosphere 2: boron trifluoride diethyl etherate / anhydrous xylene / 16 h / Inert atmosphere; Reflux 3: tert.-butylnitrite; trimethylsilylazide / acetonitrile / 0 - 20 °C View Scheme