1.1: 100 percent / H2; quinoline / Lindlar's catalyst / ethanol / 20 °C 2.1: 89 percent / pyridine; DMAP / CH2Cl2 / 0 - 20 °C 3.1: 98 percent / 1,2-lutidine / CH2Cl2 / 0 - 20 °C 4.1: 94 percent / NaI / acetone / Heating 5.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C 5.2: 68 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -30 °C 6.1: DIBALH / CH2Cl2 / -30 °C 7.1: SO3*Py; TEA / CH2Cl2 / 0 °C 8.1: LDA; ZnCl2 / tetrahydrofuran / -78 - -40 °C 8.2: tetrahydrofuran / 1 h / -50 °C 9.1: 2,6-lutidine / CH2Cl2 / 0 - 20 °C 10.1: H2O; acetic acid / 20 °C 11.1: 2,4,6-trichlorobenzoyl chloride; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C 11.2: 70 percent / H2SiF6 / 2-methyl-propan-2-ol; acetonitrile; CH2Cl2 / 24 h / 20 °C 12.1: 93 percent / oxalyl chloride; TEA; DMSO / CH2Cl2 / -78 °C 13.1: 60 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C 14.1: 92 percent / TFA / CH2Cl2 / 1 h / 0 °C 15.1: 56 percent / methyl(trifluoromethyl)dioxirane / acetonitrile / 0 °C View Scheme

1.1: 100 percent / H2; quinoline / Lindlar's catalyst / ethanol / 20 °C 2.1: 89 percent / pyridine; DMAP / CH2Cl2 / 0 - 20 °C 3.1: 98 percent / 1,2-lutidine / CH2Cl2 / 0 - 20 °C 4.1: 94 percent / NaI / acetone / Heating 5.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C 5.2: 68 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -30 °C 6.1: DIBALH / CH2Cl2 / -30 °C 7.1: SO3*Py; TEA / CH2Cl2 / 0 °C 8.1: LDA; ZnCl2 / tetrahydrofuran / -78 - -40 °C 8.2: tetrahydrofuran / 1 h / -50 °C 9.1: 2,6-lutidine / CH2Cl2 / 0 - 20 °C 10.1: H2O; acetic acid / 20 °C 11.1: 2,4,6-trichlorobenzoyl chloride; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C 11.2: 70 percent / H2SiF6 / 2-methyl-propan-2-ol; acetonitrile; CH2Cl2 / 24 h / 20 °C 12.1: 93 percent / oxalyl chloride; TEA; DMSO / CH2Cl2 / -78 °C 13.1: 60 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C 14.1: 92 percent / TFA / CH2Cl2 / 1 h / 0 °C View Scheme