1.1: 73 percent / KOH; aq. H2O2 / methanol / 14 h / 50 °C 2.1: oxalyl chloride / toluene / 28 h / 20 °C 3.1: 170 mg / H2; 2,6-lutidine / Pd/C / tetrahydrofuran / 12 h / 20 °C / 3102.97 Torr 4.1: 82 percent / diethyl ether / 3 h / -78 °C 5.1: 99 percent / aq. NaOH / methanol / 26 h / 60 °C 6.1: 92 percent / NaHCO3 / dimethylformamide / 16 h / 20 °C 7.1: 96 percent / 2,6-lutidine / CH2Cl2 / 1 h / 20 °C 8.1: aq. OsO4; N-methylmorpholine oxide / tetrahydrofuran / 16 h / 20 °C 9.1: 566 mg / NaIO4 / tetrahydrofuran; H2O / 4 h / 20 °C 10.1: 83 percent / CrCl2 / tetrahydrofuran; dioxane / 20 h / 20 °C 11.1: 94 percent / Pd(PPh3)4; CuI; triethylamine / 12 h / 20 °C 12.1: 94 percent / triethylamine; DAMP / CH2Cl2 / 2 h / 20 °C 13.1: PdCl2(PPh3)2; Bu3SnH / CH2Cl2 13.2: I2 / CH2Cl2 / 0 °C 13.3: potassium carbonate; methanol / -25 - 0 °C 14.1: 97 percent / Pd(PPh3)4; CuI / benzene / 4 h / 80 °C 15.1: 85 percent / P2O5 / 12 h / 20 °C 16.1: 77 percent / trisdimethylamino sulfonyl trimethylsilyldifluoride; water / dimethylformamide / 26 h / 0 °C 17.1: 84 percent / aq. NaOH / tetrahydrofuran / 30 h / 20 °C 18.1: 2,4,6-trichlorobenzoyl chloride; triethylamine; DMAP / tetrahydrofuran; toluene / 25.5 h / 0 - 20 °C 19.1: Me2BBr / CH2Cl2 / 1 h / -78 °C View Scheme