1: 77 percent / TBAF / tetrahydrofuran / 4 h / 20 °C 2: 1.) pyridinium dichromate, 3.) formic acid / 1.) DMF, 20 deg C, 12 h, 2.) CH2Cl2, Et2O, 3.) 20 deg C, 12 h 3: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h 4: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C 5: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C 6: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C 7: 40 percent / t-BuOK / 2 h / 20 °C View Scheme

<b>Multi-step reaction with 8 steps<br /> </b>1: p-TsOH / toluene / 12 h / Heating<br />2: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H₂O, THF, 40 deg C, 72 h<br />3: 76 percent / LiOH, 30percent H₂O₂ / methanol / 5 h / 20 &deg;C<br />4: 1.) Et₃N, isobutyl chloroformate, 2.) NaBH₄ / 1.) THF, 0 deg C, 30 min, 2.) CH₃OH, 20 deg C, 3 h<br />5: 68 percent / imidazole / dimethylformamide / 12 h / 20 &deg;C<br />6: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min<br />7: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating<br />8: 69 percent / NaH / tetrahydrofuran / 3 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 68 percent / imidazole / dimethylformamide / 12 h / 20 &deg;C<br />2: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min<br />3: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating<br />4: 69 percent / NaH / tetrahydrofuran / 3 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 1.) Et₃N, isobutyl chloroformate, 2.) NaBH₄ / 1.) THF, 0 deg C, 30 min, 2.) CH₃OH, 20 deg C, 3 h<br />2: 68 percent / imidazole / dimethylformamide / 12 h / 20 &deg;C<br />3: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min<br />4: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating<br />5: 69 percent / NaH / tetrahydrofuran / 3 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 9 steps<br /> </b>1: 79 percent / LiBr, H₂O / dimethylformamide / 12 h / Heating<br />2: p-TsOH / toluene / 12 h / Heating<br />3: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H₂O, THF, 40 deg C, 72 h<br />4: 76 percent / LiOH, 30percent H₂O₂ / methanol / 5 h / 20 &deg;C<br />5: 1.) Et₃N, isobutyl chloroformate, 2.) NaBH₄ / 1.) THF, 0 deg C, 30 min, 2.) CH₃OH, 20 deg C, 3 h<br />6: 68 percent / imidazole / dimethylformamide / 12 h / 20 &deg;C<br />7: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min<br />8: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating<br />9: 69 percent / NaH / tetrahydrofuran / 3 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 10 steps<br /> </b>1: 79 percent / NaH / tetrahydrofuran / 4 h / 20 &deg;C<br />2: 79 percent / LiBr, H₂O / dimethylformamide / 12 h / Heating<br />3: p-TsOH / toluene / 12 h / Heating<br />4: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H₂O, THF, 40 deg C, 72 h<br />5: 76 percent / LiOH, 30percent H₂O₂ / methanol / 5 h / 20 &deg;C<br />6: 1.) Et₃N, isobutyl chloroformate, 2.) NaBH₄ / 1.) THF, 0 deg C, 30 min, 2.) CH₃OH, 20 deg C, 3 h<br />7: 68 percent / imidazole / dimethylformamide / 12 h / 20 &deg;C<br />8: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min<br />9: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating<br />10: 69 percent / NaH / tetrahydrofuran / 3 h / 20 &deg;C<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4122952', constants.ctx, '0')">sodium hydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=20&deg;C;&nbsp;3&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 12 steps<br /> </b>1: 83 percent / tetrahydrofuran / 12 h / 20 &deg;C<br />2: 83 percent / 1,4-bis(methylamino)pyridine, DCC / CH₂Cl₂ / 18 h / 20 &deg;C<br />3: 79 percent / NaH / tetrahydrofuran / 4 h / 20 &deg;C<br />4: 79 percent / LiBr, H₂O / dimethylformamide / 12 h / Heating<br />5: p-TsOH / toluene / 12 h / Heating<br />6: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H₂O, THF, 40 deg C, 72 h<br />7: 76 percent / LiOH, 30percent H₂O₂ / methanol / 5 h / 20 &deg;C<br />8: 1.) Et₃N, isobutyl chloroformate, 2.) NaBH₄ / 1.) THF, 0 deg C, 30 min, 2.) CH₃OH, 20 deg C, 3 h<br />9: 68 percent / imidazole / dimethylformamide / 12 h / 20 &deg;C<br />10: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min<br />11: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating<br />12: 69 percent / NaH / tetrahydrofuran / 3 h / 20 &deg;C<br /> <br /> &nbsp;