1.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / -50 - 25 °C 2.1: tert-BuLi; CuCN; LiCl / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C 2.2: tetrahydrofuran / -78 - 25 °C 3.1: t-BuOK / tetrahydrofuran / 0.17 h / 0 °C 3.2: tetrahydrofuran / -30 - 25 °C 4.1: 1.274 g / PPTS / CH2Cl2 / 3 h / 25 °C 5.1: KO-t-Bu / tetrahydrofuran / 0.17 h / 0 °C 5.2: 76 percent / Davis reagent / -78 °C 6.1: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / -78 °C 7.1: 71 percent / TMSOTf; 4 Angstroem molecular sieves / CH2Cl2 / 5 h / -20 °C 8.1: DDQ; H2O / CH2Cl2 / 12 h / 25 °C 8.2: 81 percent / Pd(CN)2Cl2; H2O / acetone / 2 h / 25 °C View Scheme