1.1: 77 percent / CuCN 2.1: Ti(O-i-Pr)4; i-PrMgCl / diethyl ether 2.2: NBS 3.1: imidazole 4.1: DBU / CH2Cl2 4.2: 74 percent / Cs2CO3 / dimethylformamide 5.1: Pd(dppf)Cl2; KOH / tetrahydrofuran; H2O / 60 °C 6.1: TBAF / tetrahydrofuran 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: 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 (D)-(-)-tartrate; Ti(O-i-Pr)4; t-BuOOH / CH2Cl2 / -20 °C 6.1: Et3N / CH2Cl2 / 0 °C 7.1: NaI; NaHCO3 / acetone / 20 °C 8.1: 6.60 g / Zn; AcOH / methanol / sonication 9.1: i-PrMgCl; Ti(O-i-Pr)4 / diethyl ether / -78 - -50 °C 9.2: 88 percent / NBS / diethyl ether; tetrahydrofuran / -78 - 20 °C 10.1: 98 percent / imidazole / dimethylformamide / 20 °C 11.1: DBU / CH2Cl2 / 18 h / 20 °C 12.1: 1.32 g / Cs2CO3 / dimethylformamide / 20 h / 20 °C 13.1: aq. KOH; PdCl2(dppf) / tetrahydrofuran / 60 °C 14.1: TBAF / tetrahydrofuran / 20 °C View Scheme