1.1: titanium tetrachloride; zinc; 1,1-dibromomethane / tetrahydrofuran; dichloromethane / 5 h / -40 - 20 °C 2.1: K2OsO4*2H2O; methanesulfonamide; potassium carbonate; (DHQ)2PHAL; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 40 h / 0 - 20 °C 3.1: sodium chlorite; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / water; acetonitrile / 5 h / 20 °C / pH 6.7 / aq. phosphate buffer 4.1: hydrogenchloride / water / 10 h / Reflux 5.1: potassium tert-butylate / ethylene glycol dimethyl ether / 0.5 h / 20 °C 5.2: 12 h / Reflux 6.1: bis(acetato)bis(triphenylphosphine)palladium(0); potassium acetate / acetonitrile / 12 h / 100 °C / Inert atmosphere View Scheme

1: titanium tetrachloride; zinc; 1,1-dibromomethane / tetrahydrofuran; dichloromethane / 5 h / -40 - 20 °C 2: K2OsO4*2H2O; methanesulfonamide; potassium carbonate; (DHQ)2PHAL; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 40 h / 0 - 20 °C 3: sodium chlorite; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / water; acetonitrile / 5 h / 20 °C / pH 6.7 / aq. phosphate buffer 4: hydrogenchloride / water / 10 h / Reflux View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '7054643', constants.ctx, '0')">pyridinium chlorochromate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=20&deg;C;&nbsp;12&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: potassium borohydride; lithium chloride / tetrahydrofuran / 12 h / 35 &deg;C<br />2: 1H-imidazole / dichloromethane / 1 h / 20 &deg;C<br />3: pyridinium chlorochromate / dichloromethane / 12 h / 20 &deg;C<br /> <br /> &nbsp;