1.1: 81 percent / diisopropylethylamine / CH2Cl2 / 28 h / 20 °C 2.1: DIBAL-H / CH2Cl2; petroleum ether / 1 h / -78 °C 3.1: 2-methyl-2-butene; NaH2PO4; NaClO2 / H2O; 2-methyl-propan-2-ol / 1 h / 0 °C 4.1: K2CO3 / dimethylformamide / 3.5 h / 20 °C 5.1: H2 / Pd/C / tetrahydrofuran; ethanol / 3 h / 10343.2 Torr 6.1: 89 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 7.1: 86 percent / potassium tert-butoxide / tetrahydrofuran / 18 h / -70 - 20 °C 8.1: 91 percent / c. HCl / methanol / 0.5 h / 20 °C 9.1: 94 percent / Pd(PPh3)4; CuI; triethylamine / 12 h / 20 °C 10.1: 94 percent / triethylamine; DAMP / CH2Cl2 / 2 h / 20 °C 11.1: PdCl2(PPh3)2; Bu3SnH / CH2Cl2 11.2: I2 / CH2Cl2 / 0 °C 11.3: potassium carbonate; methanol / -25 - 0 °C 12.1: 97 percent / Pd(PPh3)4; CuI / benzene / 4 h / 80 °C 13.1: 85 percent / P2O5 / 12 h / 20 °C 14.1: 77 percent / trisdimethylamino sulfonyl trimethylsilyldifluoride; water / dimethylformamide / 26 h / 0 °C 15.1: 84 percent / aq. NaOH / tetrahydrofuran / 30 h / 20 °C 16.1: 2,4,6-trichlorobenzoyl chloride; triethylamine; DMAP / tetrahydrofuran; toluene / 25.5 h / 0 - 20 °C 17.1: Me2BBr / CH2Cl2 / 1 h / -78 °C View Scheme