1: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 2: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 3: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 4: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 5: 64 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 6: 88 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 2: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 3: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 4: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 5: 58 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 6: 90 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 2: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 3: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 4: 76 percent / LiAlH4 / diethyl ether / 48 h / Heating 5: MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 6: p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1: 95 percent / LiAlH₄ / diethyl ether / 0 &deg;C<br />2: 81 percent / CrO₃, pyridine / CH₂Cl₂ / Ambient temperature<br />3: 80 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 80 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 98 percent / H₂, NaOH / 10percent Pd/C / H₂O / 12 h / 22501.8 Torr<br />2: 98 percent / conc.H₂SO₄ / Heating<br />3: 1) NaH, 2) tetrabutylammonium iodide / 1) THF, 0 deg C, 0.5 h, 2) 0 deg C<br />4: 95 percent / LiAlH₄ / diethyl ether / 0 &deg;C<br />5: 81 percent / CrO₃, pyridine / CH₂Cl₂ / Ambient temperature<br />6: 80 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 99 percent / methanol / Heating<br />2: 98 percent / imidazole / dimethylformamide / 24 h / Ambient temperature<br />3: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) -50 deg C<br />4: DIBAL / tetrahydrofuran; toluene / 2 h / -78 &deg;C<br />5: 1) Zn-powder, 2) trimethylsilyl chloride / 1) THF, r.t., 15 min, 2) r.t., 45 min<br />6: 1) Me₃OBF₄, 2) aq.Na₂CO₃ / 1) CH₂Cl₂, r.t., 2 h, 2) 6 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 98 percent / imidazole / dimethylformamide / 24 h / Ambient temperature<br />2: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) -50 deg C<br />3: DIBAL / tetrahydrofuran; toluene / 2 h / -78 &deg;C<br />4: 1) Zn-powder, 2) trimethylsilyl chloride / 1) THF, r.t., 15 min, 2) r.t., 45 min<br />5: 1) Me₃OBF₄, 2) aq.Na₂CO₃ / 1) CH₂Cl₂, r.t., 2 h, 2) 6 h<br /> <br /> &nbsp;