tetrabutyl ammonium fluoride in tetrahydrofuran T=55°C; 13 h;

<b>Multi-step reaction with 7 steps<br /> </b>1: 56 percent / Et₂Zn / toluene / 8 h / Ambient temperature<br />2: DIBAL / CH₂Cl₂ <br />3: imidazole / dimethylformamide / 10 h / 55 &deg;C<br />4: 61 percent / CuBr / chlorobenzene / 4 h / 115 &deg;C<br />5: 96 percent / aq. NaOH / methanol; tetrahydrofuran<br />6: 93 percent / Li, NH₃ / tetrahydrofuran / 2 h / -78 &deg;C<br />7: 1.) PDC, 2.) NaClO₂, NaH₂PO₄ / 1.) 5 h, 2.) 2-methyl-2-butene, t-BuOH, 20 min<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: imidazole / dimethylformamide / 10 h / 55 &deg;C<br />2: 61 percent / CuBr / chlorobenzene / 4 h / 115 &deg;C<br />3: 96 percent / aq. NaOH / methanol; tetrahydrofuran<br />4: 93 percent / Li, NH₃ / tetrahydrofuran / 2 h / -78 &deg;C<br />5: 1.) PDC, 2.) NaClO₂, NaH₂PO₄ / 1.) 5 h, 2.) 2-methyl-2-butene, t-BuOH, 20 min<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1: 72 percent / Pb(OAc)4, Cu(OAc)2, pyridine / acetonitrile / 80 &deg;C<br />2: 56 percent / Et₂Zn / toluene / 8 h / Ambient temperature<br />3: DIBAL / CH₂Cl₂ <br />4: imidazole / dimethylformamide / 10 h / 55 &deg;C<br />5: 61 percent / CuBr / chlorobenzene / 4 h / 115 &deg;C<br />6: 96 percent / aq. NaOH / methanol; tetrahydrofuran<br />7: 93 percent / Li, NH₃ / tetrahydrofuran / 2 h / -78 &deg;C<br />8: 1.) PDC, 2.) NaClO₂, NaH₂PO₄ / 1.) 5 h, 2.) 2-methyl-2-butene, t-BuOH, 20 min<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 61 percent / CuBr / chlorobenzene / 4 h / 115 &deg;C<br />2: 96 percent / aq. NaOH / methanol; tetrahydrofuran<br />3: 93 percent / Li, NH₃ / tetrahydrofuran / 2 h / -78 &deg;C<br />4: 1.) PDC, 2.) NaClO₂, NaH₂PO₄ / 1.) 5 h, 2.) 2-methyl-2-butene, t-BuOH, 20 min<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 96 percent / aq. NaOH / methanol; tetrahydrofuran<br />2: 93 percent / Li, NH₃ / tetrahydrofuran / 2 h / -78 &deg;C<br />3: 1.) PDC, 2.) NaClO₂, NaH₂PO₄ / 1.) 5 h, 2.) 2-methyl-2-butene, t-BuOH, 20 min<br /> <br /> &nbsp;