sodium-mercury amalgam (10); water in methanol Inert atmosphere; optical yield given as percent ee;

1: 95 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / 0 °C 2: (-)-diisopropyl tartrate; t-BuOOH; 4 Angstroem molecular sieves / Ti(OPr-i)4 / CH2Cl2; 2,2,4-trimethyl-pentane / 2 h / -25 °C 3: 64 percent / aq. NaOH / 2.5 h / 70 °C 4: 100 percent / Et3N / CH2Cl2 / 12 h / 20 °C 5: 71 percent / NaI / butan-2-one / 4 h / Heating 6: 69 percent / Bu3SnH; AIBN / toluene / 2 h / 80 °C 7: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C 8: Na(Hg) / methanol; H2O / 12 h View Scheme

1: (-)-diisopropyl tartrate; t-BuOOH; 4 Angstroem molecular sieves / Ti(OPr-i)4 / CH2Cl2; 2,2,4-trimethyl-pentane / 2 h / -25 °C 2: 64 percent / aq. NaOH / 2.5 h / 70 °C 3: 100 percent / Et3N / CH2Cl2 / 12 h / 20 °C 4: 71 percent / NaI / butan-2-one / 4 h / Heating 5: 69 percent / Bu3SnH; AIBN / toluene / 2 h / 80 °C 6: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C 7: Na(Hg) / methanol; H2O / 12 h View Scheme

1: 81 percent / Et3N; LiBr / tetrahydrofuran / 4 h / 20 °C 2: 95 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / 0 °C 3: (-)-diisopropyl tartrate; t-BuOOH; 4 Angstroem molecular sieves / Ti(OPr-i)4 / CH2Cl2; 2,2,4-trimethyl-pentane / 2 h / -25 °C 4: 64 percent / aq. NaOH / 2.5 h / 70 °C 5: 100 percent / Et3N / CH2Cl2 / 12 h / 20 °C 6: 71 percent / NaI / butan-2-one / 4 h / Heating 7: 69 percent / Bu3SnH; AIBN / toluene / 2 h / 80 °C 8: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C 9: Na(Hg) / methanol; H2O / 12 h View Scheme

1: 69 percent / Bu3SnH; AIBN / toluene / 2 h / 80 °C 2: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C 3: Na(Hg) / methanol; H2O / 12 h View Scheme

1: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C 2: Na(Hg) / methanol; H2O / 12 h View Scheme

1: 64 percent / aq. NaOH / 2.5 h / 70 °C 2: 100 percent / Et3N / CH2Cl2 / 12 h / 20 °C 3: 71 percent / NaI / butan-2-one / 4 h / Heating 4: 69 percent / Bu3SnH; AIBN / toluene / 2 h / 80 °C 5: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C 6: Na(Hg) / methanol; H2O / 12 h View Scheme

1: 97 percent / K2CO3 / tetrahydrofuran; H2O; methanol / 2.5 h 2: 64 percent / aq. NaOH / 2.5 h / 70 °C 3: 100 percent / Et3N / CH2Cl2 / 12 h / 20 °C 4: 71 percent / NaI / butan-2-one / 4 h / Heating 5: 69 percent / Bu3SnH; AIBN / toluene / 2 h / 80 °C 6: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C 7: Na(Hg) / methanol; H2O / 12 h View Scheme

1: 100 percent / Et3N / CH2Cl2 / 12 h / 20 °C 2: 71 percent / NaI / butan-2-one / 4 h / Heating 3: 69 percent / Bu3SnH; AIBN / toluene / 2 h / 80 °C 4: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C 5: Na(Hg) / methanol; H2O / 12 h View Scheme

1: 71 percent / NaI / butan-2-one / 4 h / Heating 2: 69 percent / Bu3SnH; AIBN / toluene / 2 h / 80 °C 3: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C 4: Na(Hg) / methanol; H2O / 12 h View Scheme