1: 1) t-BuOK / 1) THF, 55 deg C (bath temp.), 1 h, 2) THF, reflux, 1 h 2: pyridine, 4-(dimethylamino)pyridine (DMAP) / tetrahydrofuran / 1 h / Ambient temperature 3: 91 percent / EtAlCl2 / CH2Cl2; hexane / 2.5 h / Ambient temperature 4: 96 percent / H2 / 5percent Pt-C / ethyl acetate / 0.83 h / Ambient temperature 5: 30percent KOH / tetrahydrofuran; methanol / 2.5 h / Heating 6: 1) i-Pr2NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h 7: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / Ambient temperature 8: 90 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 5 h / Ambient temperature 9: 1) PhLi / 1) cyclohexane, Et2O, THF, r.t., 30 min, 2) THF, r.t., 30 min 10: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature 11: 1) Hg(OAc)2, 2) NaBH4, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min 12: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature 13: 77 percent / 1,2-dichloro-ethane / 1) reflux, 2 h, 2) r.t., 12 h, 3) reflux, 1 h 14: 82 percent / Bu3SnH / toluene / 1 h / Heating 15: 75 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 5 h / Ambient temperature View Scheme