1.1: 98 percent / lithium aluminum hydride / 1 h / 20 °C 2.1: 86 percent / chromium(VI) oxide; pyridine / CHCl3 / 12 h / 20 °C 3.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 3.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 4.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C 5.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 6.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 7.1: pyridine / CHCl3 / 3 h / 20 °C 8.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C 9.1: aq. hydrobromic acid / CHCl3; acetic acid / 1.5 h / 20 °C 9.2: 44 percent / tributyltin hydride; α,α'-azobis(isobutyronitrile) / benzene / 1 h / Heating View Scheme

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

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

1: 1) i-Pr2NEt / 1) DMF, THF, r.t., 30 min, 2) 60 deg C (bath temp.), 4.5 h 2: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / Ambient temperature 3: 90 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 5 h / Ambient temperature 4: 1) PhLi / 1) cyclohexane, Et2O, THF, r.t., 30 min, 2) THF, r.t., 30 min 5: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature 6: 1) Hg(OAc)2, 2) NaBH4, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min 7: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature 8: 77 percent / 1,2-dichloro-ethane / 1) reflux, 2 h, 2) r.t., 12 h, 3) reflux, 1 h 9: 82 percent / Bu3SnH / toluene / 1 h / Heating 10: 75 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 5 h / Ambient temperature View Scheme

1: 90 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 5 h / Ambient temperature 2: 1) PhLi / 1) cyclohexane, Et2O, THF, r.t., 30 min, 2) THF, r.t., 30 min 3: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature 4: 1) Hg(OAc)2, 2) NaBH4, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min 5: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature 6: 77 percent / 1,2-dichloro-ethane / 1) reflux, 2 h, 2) r.t., 12 h, 3) reflux, 1 h 7: 82 percent / Bu3SnH / toluene / 1 h / Heating 8: 75 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 5 h / Ambient temperature View Scheme

1: 77 percent / 1,2-dichloro-ethane / 1) reflux, 2 h, 2) r.t., 12 h, 3) reflux, 1 h 2: 82 percent / Bu3SnH / toluene / 1 h / Heating 3: 75 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 5 h / Ambient temperature View Scheme

1: 1) PhLi / 1) cyclohexane, Et2O, THF, r.t., 30 min, 2) THF, r.t., 30 min 2: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature 3: 1) Hg(OAc)2, 2) NaBH4, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min 4: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature 5: 77 percent / 1,2-dichloro-ethane / 1) reflux, 2 h, 2) r.t., 12 h, 3) reflux, 1 h 6: 82 percent / Bu3SnH / toluene / 1 h / Heating 7: 75 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 5 h / Ambient temperature View Scheme

1: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature 2: 1) Hg(OAc)2, 2) NaBH4, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min 3: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature 4: 77 percent / 1,2-dichloro-ethane / 1) reflux, 2 h, 2) r.t., 12 h, 3) reflux, 1 h 5: 82 percent / Bu3SnH / toluene / 1 h / Heating 6: 75 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 5 h / Ambient temperature View Scheme

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

1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / Ambient temperature 2: 90 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 5 h / Ambient temperature 3: 1) PhLi / 1) cyclohexane, Et2O, THF, r.t., 30 min, 2) THF, r.t., 30 min 4: 90 percent / 6 M HCl / tetrahydrofuran / 31 h / Ambient temperature 5: 1) Hg(OAc)2, 2) NaBH4, 3 M NaOH / 1) THF, r.t., 5 h, 2) r.t., 15 min 6: 91 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature 7: 77 percent / 1,2-dichloro-ethane / 1) reflux, 2 h, 2) r.t., 12 h, 3) reflux, 1 h 8: 82 percent / Bu3SnH / toluene / 1 h / Heating 9: 75 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 5 h / Ambient temperature View Scheme