tetrabutyl ammonium fluoride; acetic acid in tetrahydrofuran

<b>Multi-step reaction with 14 steps<br /> </b>1: benzene / Ambient temperature<br />2: H₂ / Pd-C / ethanol / 1551.4 Torr / Ambient temperature<br />3: conc. HCl / 0 &deg;C<br />4: H₂SO₄, CuSO / Ambient temperature<br />5: 1.) BF₃*Et₂O, HgO (red) 2.) NaBH₄ / 1.) THF, r.t. 2.) EtOH, r.t.<br />6: Ph₃P, CCl₄ / Heating<br />7: LiOH / H₂O; 1,2-dimethoxy-ethane / Ambient temperature<br />8: LDA / tetrahydrofuran / -25 &deg;C<br />9: NaH / tetrahydrofuran / Ambient temperature<br />10: 1.5 N HCl / H₂O; tetrahydrofuran / Ambient temperature<br />11: diethyl ether<br />12: benzene / Ambient temperature<br />13: CuCl, TMEDA, O₂ / acetone / 0.02 h / Ambient temperature<br />14: DDQ / H₂O; CH₂Cl₂ / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 1.) O₃, 2.) Ac₂O, NEt₃ / 1.) CH₂Cl₂, -78 deg C, 2.) benzene<br />2: 68 percent / tetrahydrofuran / -78 &deg;C<br />3: 36 percent / Ti(OiPr)4, L-(+)-DIPT, tBuOOH, 3 Angstroem sieves / CH₂Cl₂ / -20 deg C to room temperature<br />4: 66 percent / acetonitrile / 168 h / Ambient temperature<br />5: 69 percent / BF₃*Et₂O / diethyl ether / -20 &deg;C<br />6: 1.) oxalyl chloride, DMSO, 2.) NEt₃ / 1.) THF, -60 deg C to -35 deg C, 2.) -35 deg C to room temperature<br />7: 1.) methyl lithium-lithium bromide / 1.) THF, -78 deg C to room temperature, 2.) THF, -78 deg C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 68 percent / tetrahydrofuran / -78 &deg;C<br />2: 36 percent / Ti(OiPr)4, L-(+)-DIPT, tBuOOH, 3 Angstroem sieves / CH₂Cl₂ / -20 deg C to room temperature<br />3: 66 percent / acetonitrile / 168 h / Ambient temperature<br />4: 69 percent / BF₃*Et₂O / diethyl ether / -20 &deg;C<br />5: 1.) oxalyl chloride, DMSO, 2.) NEt₃ / 1.) THF, -60 deg C to -35 deg C, 2.) -35 deg C to room temperature<br />6: 1.) methyl lithium-lithium bromide / 1.) THF, -78 deg C to room temperature, 2.) THF, -78 deg C<br /> <br /> &nbsp;