1: 1.) (COCl)2, 2.) Et3N / 1.) DMSO, 2.) CH2Cl2, -78 deg C 2: tetrahydrofuran 3: 76 percent / TiCl4 / CH2Cl2 / -78 °C 4: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O 5: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN 6: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C View Scheme

<b>Multi-step reaction with 6 steps<br /> </b>1: 92 percent / DIBAL / CH₂Cl₂ / -78 &deg;C<br />2: 87 percent / PPTS / methanol<br />3: 96 percent / Bu₄NF / tetrahydrofuran<br />4: 1.) BuLi / 1.) THF, -78 deg C<br />5: toluene / Irradiation<br />6: 1.) BH₃*DMS, 2.) H₂O₂, 6M NaOH / 1.) THF<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 87 percent / PPTS / methanol<br />2: 96 percent / Bu₄NF / tetrahydrofuran<br />3: 1.) BuLi / 1.) THF, -78 deg C<br />4: toluene / Irradiation<br />5: 1.) BH₃*DMS, 2.) H₂O₂, 6M NaOH / 1.) THF<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11342940', constants.ctx, '0')">sodium hydroxide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1918603', constants.ctx, '0')">dimethylsulfide borane complex</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587191', constants.ctx, '0')">dihydrogen peroxide</a> <br />&nbsp;1.) THF;&nbsp;&nbsp;Yield given. Multistep reaction;&nbsp;<br /> &nbsp;