1: 98 percent / Bu3SnH; 1,1'-azobis(cyclohexane carbonitrile) / benzene / 16 h / Heating 2: 71 percent / H2 / Pd/C / methanol / 7 h / 20 °C View Scheme

<b>Multi-step reaction with 6 steps<br /> </b>1: 94 percent / DCC / DMAP / CH₂Cl₂ / 12 h / 20 &deg;C<br />2: DIBAL-H / -78 &deg;C<br />3: DMAP; pyridine; DIBAL-H / CH₂Cl₂; hexane / -78 - 0 &deg;C<br />4: 84 percent / SnBr₄ / CH₂Cl₂ / 1.3 h / -78 &deg;C<br />5: K₂CO₃ / methanol / 3 h / Heating<br />6: 217 mg / K₂CO₃ / acetone / 12 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: DIBAL-H / -78 &deg;C<br />2: DMAP; pyridine; DIBAL-H / CH₂Cl₂; hexane / -78 - 0 &deg;C<br />3: 84 percent / SnBr₄ / CH₂Cl₂ / 1.3 h / -78 &deg;C<br />4: K₂CO₃ / methanol / 3 h / Heating<br />5: 217 mg / K₂CO₃ / acetone / 12 h<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '14390453', constants.ctx, '0')">indium tribromide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1731135', constants.ctx, '0')">trimethylsilyl bromide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-78&deg;C;&nbsp;Prins cyclization;&nbsp;1&nbsp;h;&nbsp;<br /> &nbsp;