1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: 99 percent / Mg; 1,2-dibromoethane / diethyl ether / 3.5 h / 20 °C 3.1: Et3N / CH2Cl2 / 0.17 h / 0 °C 4.1: 84 percent / LiBr / acetone; CH2Cl2 / 1.8 h / 20 °C 5.1: CuI; Et3N / diethyl ether; dimethylformamide / 20 °C 5.2: 60 percent / diethyl ether; dimethylformamide / 18 h / 20 °C 6.1: 68 percent / H2; Pb(OAc)2 / Pd/CaCO3 / hexane / 28 h / 20 °C 7.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 8.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 9.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 9.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 10.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 11.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating 12.1: 78 percent / dimethyldioxirane / CH2Cl2 / -50 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: 99 percent / Mg; 1,2-dibromoethane / diethyl ether / 3.5 h / 20 °C 3.1: Et3N / CH2Cl2 / 0.17 h / 0 °C 4.1: 84 percent / LiBr / acetone; CH2Cl2 / 1.8 h / 20 °C 5.1: CuI; Et3N / diethyl ether; dimethylformamide / 20 °C 5.2: 60 percent / diethyl ether; dimethylformamide / 18 h / 20 °C 6.1: 68 percent / H2; Pb(OAc)2 / Pd/CaCO3 / hexane / 28 h / 20 °C 7.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 8.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 9.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 9.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 10.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 11.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating View Scheme