1: 71 percent / O2 / PdCl2, CuCl / dimethylformamide; H2O 2: 1.) KH, TMSCl, 2.) Et3N / 2.) Pd(OAc)2 / 2.) CH3CN 3: 76 percent / Na(Hg), Na2HPO4 / methanol / 0.17 h / -40 °C View Scheme

<b>Multi-step reaction with 9 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 />7: 1.) (COCl)2, 2.) Et₃N / 1.) DMSO, 2.) CH₂Cl₂, -78 deg C<br />8: tetrahydrofuran<br />9: 76 percent / TiCl₄ / CH₂Cl₂ / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 1.) BH₃*DMS, 2.) H₂O₂, 6M NaOH / 1.) THF<br />2: 1.) (COCl)2, 2.) Et₃N / 1.) DMSO, 2.) CH₂Cl₂, -78 deg C<br />3: tetrahydrofuran<br />4: 76 percent / TiCl₄ / CH₂Cl₂ / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 1.) (COCl)2, 2.) Et₃N / 1.) DMSO, 2.) CH₂Cl₂, -78 deg C<br />2: tetrahydrofuran<br />3: 76 percent / TiCl₄ / CH₂Cl₂ / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 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 />6: 1.) (COCl)2, 2.) Et₃N / 1.) DMSO, 2.) CH₂Cl₂, -78 deg C<br />7: tetrahydrofuran<br />8: 76 percent / TiCl₄ / CH₂Cl₂ / -78 &deg;C<br /> <br /> &nbsp;