1: 1) Hg(OAc)2, 2) NaBH4, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min 2: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature 3: 77 percent / 1,2-dichloro-ethane / 1) reflux, 2 h, 2) r.t., 12 h, 3) reflux, 1 h 4: 82 percent / Bu3SnH / toluene / 1 h / Heating 5: 75 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 5 h / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098214', constants.ctx, '0')">hydrogenchloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />31&nbsp;h;&nbsp;&nbsp;Ambient temperature;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 9 steps<br /> </b>1: pyridine, 4-(dimethylamino)pyridine (DMAP) / tetrahydrofuran / 1 h / Ambient temperature<br />2: 91 percent / EtAlCl₂ / CH₂Cl₂; hexane / 2.5 h / Ambient temperature<br />3: 96 percent / H₂ / 5percent Pt-C / ethyl acetate / 0.83 h / Ambient temperature<br />4: 30percent KOH / tetrahydrofuran; methanol / 2.5 h / Heating<br />5: 1) i-Pr₂NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h<br />6: 91 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / Ambient temperature<br />7: 90 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 5 h / Ambient temperature<br />8: 1) PhLi / 1) cyclohexane, Et₂O, THF, r.t., 30 min, 2) THF, r.t., 30 min<br />9: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 10 steps<br /> </b>1: 1) t-BuOK / 1) THF, 55 deg C (bath temp.), 1 h, 2) THF, reflux, 1 h<br />2: pyridine, 4-(dimethylamino)pyridine (DMAP) / tetrahydrofuran / 1 h / Ambient temperature<br />3: 91 percent / EtAlCl₂ / CH₂Cl₂; hexane / 2.5 h / Ambient temperature<br />4: 96 percent / H₂ / 5percent Pt-C / ethyl acetate / 0.83 h / Ambient temperature<br />5: 30percent KOH / tetrahydrofuran; methanol / 2.5 h / Heating<br />6: 1) i-Pr₂NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h<br />7: 91 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / Ambient temperature<br />8: 90 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 5 h / Ambient temperature<br />9: 1) PhLi / 1) cyclohexane, Et₂O, THF, r.t., 30 min, 2) THF, r.t., 30 min<br />10: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1: 91 percent / EtAlCl₂ / CH₂Cl₂; hexane / 2.5 h / Ambient temperature<br />2: 96 percent / H₂ / 5percent Pt-C / ethyl acetate / 0.83 h / Ambient temperature<br />3: 30percent KOH / tetrahydrofuran; methanol / 2.5 h / Heating<br />4: 1) i-Pr₂NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h<br />5: 91 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / Ambient temperature<br />6: 90 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 5 h / Ambient temperature<br />7: 1) PhLi / 1) cyclohexane, Et₂O, THF, r.t., 30 min, 2) THF, r.t., 30 min<br />8: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 96 percent / H₂ / 5percent Pt-C / ethyl acetate / 0.83 h / Ambient temperature<br />2: 30percent KOH / tetrahydrofuran; methanol / 2.5 h / Heating<br />3: 1) i-Pr₂NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h<br />4: 91 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / Ambient temperature<br />5: 90 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 5 h / Ambient temperature<br />6: 1) PhLi / 1) cyclohexane, Et₂O, THF, r.t., 30 min, 2) THF, r.t., 30 min<br />7: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 1) i-Pr₂NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h<br />2: 91 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / Ambient temperature<br />3: 90 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 5 h / Ambient temperature<br />4: 1) PhLi / 1) cyclohexane, Et₂O, THF, r.t., 30 min, 2) THF, r.t., 30 min<br />5: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 90 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 5 h / Ambient temperature<br />2: 1) PhLi / 1) cyclohexane, Et₂O, THF, r.t., 30 min, 2) THF, r.t., 30 min<br />3: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 1) PhLi / 1) cyclohexane, Et₂O, THF, r.t., 30 min, 2) THF, r.t., 30 min<br />2: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 30percent KOH / tetrahydrofuran; methanol / 2.5 h / Heating<br />2: 1) i-Pr₂NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h<br />3: 91 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / Ambient temperature<br />4: 90 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 5 h / Ambient temperature<br />5: 1) PhLi / 1) cyclohexane, Et₂O, THF, r.t., 30 min, 2) THF, r.t., 30 min<br />6: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature<br /> <br /> &nbsp;