1: 1.) n-BuLI, 2.) / 1.) dioxane, from 5 deg C to 25 deg C, 1.5 h, 2.) dioxane, reflux, 40 h 2: 99 percent / NaHCO3, H2 / 5percent Rh/C / ethyl acetate / 18 h / 760 Torr 3: 87 percent / AG 50W-X4 / CH2Cl2; methanol / 1 h / Ambient temperature 4: 93 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature 5: 98 percent / CH2Cl2 / 18 h / Ambient temperature 6: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1: 1.) n-BuLI, 2.) / 1.) dioxane, from 5 deg C to 25 deg C, 1.5 h, 2.) dioxane, reflux, 40 h 2: 99 percent / NaHCO3, H2 / 5percent Rh/C / ethyl acetate / 18 h / 760 Torr 3: 87 percent / AG 50W-X4 / CH2Cl2; methanol / 1 h / Ambient temperature 4: 93 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature 5: 98 percent / CH2Cl2 / 18 h / Ambient temperature 6: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1: 99 percent / NaHCO3, H2 / 5percent Rh/C / ethyl acetate / 18 h / 760 Torr 2: 87 percent / AG 50W-X4 / CH2Cl2; methanol / 1 h / Ambient temperature 3: 93 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature 4: 98 percent / CH2Cl2 / 18 h / Ambient temperature 5: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1: 95 percent / pyridine / 23 h / 0 - 20 °C 2: 1.) n-BuLI, 2.) / 1.) dioxane, from 5 deg C to 25 deg C, 1.5 h, 2.) dioxane, reflux, 40 h 3: 99 percent / NaHCO3, H2 / 5percent Rh/C / ethyl acetate / 18 h / 760 Torr 4: 87 percent / AG 50W-X4 / CH2Cl2; methanol / 1 h / Ambient temperature 5: 93 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature 6: 98 percent / CH2Cl2 / 18 h / Ambient temperature 7: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: BF3*Et2O / tetrahydrofuran; hexane / -78 - 20 °C 1.3: 82 percent / hydrochloric acid / tetrahydrofuran / 1 h / 20 °C 2.1: 96 percent / porcine pancreatic lipase / 72 h / 20 °C 3.1: imidazole / dimethylformamide / 12 h / 20 °C 4.1: 27.8 g / Red-Al / diethyl ether; toluene / 1 h / 0 °C 5.1: diisopropyl (L)-(+)-tartrate; Ti(O-i-Pr)4; t-BuOOH / CH2Cl2 / 24 h / -20 °C 6.1: Et3N / CH2Cl2 / 1 h / 0 °C 7.1: NaI; NaHCO3 / acetone / 20 h / 20 °C 8.1: 21.7 g / Zn; AcOH / methanol / 1 h / sonication 9.1: i-PrMgCl; Ti(O-i-Pr)4 / diethyl ether / -78 - -50 °C 9.2: 51 percent / NBS / diethyl ether; tetrahydrofuran / -78 - 20 °C 10.1: 96 percent / imidazole / dimethylformamide / 12 h / 20 °C 11.1: DBU / toluene / 20 h / 70 °C 12.1: 1.16 g / Cs2CO3 / dimethylformamide / 12 h / 20 °C 13.1: aq. KOH; PdCl2(dppf) / tetrahydrofuran / 24 h / 60 °C 14.1: 68.3 mg / TBAF / tetrahydrofuran / 24 h / 20 °C View Scheme

1.1: diisopropyl (L)-(+)-tartrate; Ti(O-i-Pr)4; t-BuOOH / CH2Cl2 / 24 h / -20 °C 2.1: Et3N / CH2Cl2 / 1 h / 0 °C 3.1: NaI; NaHCO3 / acetone / 20 h / 20 °C 4.1: 21.7 g / Zn; AcOH / methanol / 1 h / sonication 5.1: i-PrMgCl; Ti(O-i-Pr)4 / diethyl ether / -78 - -50 °C 5.2: 51 percent / NBS / diethyl ether; tetrahydrofuran / -78 - 20 °C 6.1: 96 percent / imidazole / dimethylformamide / 12 h / 20 °C 7.1: DBU / toluene / 20 h / 70 °C 8.1: 1.16 g / Cs2CO3 / dimethylformamide / 12 h / 20 °C 9.1: aq. KOH; PdCl2(dppf) / tetrahydrofuran / 24 h / 60 °C 10.1: 68.3 mg / TBAF / tetrahydrofuran / 24 h / 20 °C View Scheme

1.1: i-PrMgCl; Ti(O-i-Pr)4 / diethyl ether / -78 - -50 °C 1.2: 51 percent / NBS / diethyl ether; tetrahydrofuran / -78 - 20 °C 2.1: 96 percent / imidazole / dimethylformamide / 12 h / 20 °C 3.1: DBU / toluene / 20 h / 70 °C 4.1: 1.16 g / Cs2CO3 / dimethylformamide / 12 h / 20 °C 5.1: aq. KOH; PdCl2(dppf) / tetrahydrofuran / 24 h / 60 °C 6.1: 68.3 mg / TBAF / tetrahydrofuran / 24 h / 20 °C View Scheme

1.1: 96 percent / porcine pancreatic lipase / 72 h / 20 °C 2.1: imidazole / dimethylformamide / 12 h / 20 °C 3.1: 27.8 g / Red-Al / diethyl ether; toluene / 1 h / 0 °C 4.1: diisopropyl (L)-(+)-tartrate; Ti(O-i-Pr)4; t-BuOOH / CH2Cl2 / 24 h / -20 °C 5.1: Et3N / CH2Cl2 / 1 h / 0 °C 6.1: NaI; NaHCO3 / acetone / 20 h / 20 °C 7.1: 21.7 g / Zn; AcOH / methanol / 1 h / sonication 8.1: i-PrMgCl; Ti(O-i-Pr)4 / diethyl ether / -78 - -50 °C 8.2: 51 percent / NBS / diethyl ether; tetrahydrofuran / -78 - 20 °C 9.1: 96 percent / imidazole / dimethylformamide / 12 h / 20 °C 10.1: DBU / toluene / 20 h / 70 °C 11.1: 1.16 g / Cs2CO3 / dimethylformamide / 12 h / 20 °C 12.1: aq. KOH; PdCl2(dppf) / tetrahydrofuran / 24 h / 60 °C 13.1: 68.3 mg / TBAF / tetrahydrofuran / 24 h / 20 °C View Scheme

1.1: imidazole / dimethylformamide / 12 h / 20 °C 2.1: 27.8 g / Red-Al / diethyl ether; toluene / 1 h / 0 °C 3.1: diisopropyl (L)-(+)-tartrate; Ti(O-i-Pr)4; t-BuOOH / CH2Cl2 / 24 h / -20 °C 4.1: Et3N / CH2Cl2 / 1 h / 0 °C 5.1: NaI; NaHCO3 / acetone / 20 h / 20 °C 6.1: 21.7 g / Zn; AcOH / methanol / 1 h / sonication 7.1: i-PrMgCl; Ti(O-i-Pr)4 / diethyl ether / -78 - -50 °C 7.2: 51 percent / NBS / diethyl ether; tetrahydrofuran / -78 - 20 °C 8.1: 96 percent / imidazole / dimethylformamide / 12 h / 20 °C 9.1: DBU / toluene / 20 h / 70 °C 10.1: 1.16 g / Cs2CO3 / dimethylformamide / 12 h / 20 °C 11.1: aq. KOH; PdCl2(dppf) / tetrahydrofuran / 24 h / 60 °C 12.1: 68.3 mg / TBAF / tetrahydrofuran / 24 h / 20 °C View Scheme

1: aq. KOH; PdCl2(dppf) / tetrahydrofuran / 24 h / 60 °C 2: 68.3 mg / TBAF / tetrahydrofuran / 24 h / 20 °C View Scheme