1: 1) LDA / 1) THF, -78 deg C, 15 min; -30 deg C, 1.5 h, 2) THF, -78 deg C, 15 min; -40 deg C, 1 h 2: 0.940 g / 4-(dimethylamino)pyridine, 1-ethyl-3-((dimethylamino)propyl)carbodiimide hydrochloride / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h 3: 46 percent / RuCl2(=CHPh)(PCy3)2 / CH2Cl2 / 20 h / 25 °C 4: 90 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 0 °C 5: 62 percent / Na2EDTA, 1,1,1-trifluoroacetone, Oxone, NaHCO3 / acetonitrile; H2O / 0 °C View Scheme

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 1.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 2.1: pyridine / CH2Cl2 / 1 h / 0 °C 3.1: CH2Cl2 / 5 h / 20 °C 4.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 5.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 6.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 7.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 8.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C 9.1: 30 percent / m-CPBA / CHCl3 / 5 h / -10 - 0 °C View Scheme

1.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / |Inert atmosphere 1.2: 1 h / -78 °C / |Inert atmosphere 1.3: 3 h / -78 - 20 °C / |Inert atmosphere 2.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / |Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 4.2: 20 °C / |Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / |Inert atmosphere 6.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 °C View Scheme

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 1.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 2.1: pyridine / CH2Cl2 / 1 h / 0 °C 3.1: CH2Cl2 / 5 h / 20 °C 4.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 5.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 6.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 7.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 8.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

1: 1) LDA / 1) THF, -78 deg C, 15 min; -30 deg C, 1.5 h, 2) THF, -78 deg C, 15 min; -40 deg C, 1 h 2: 0.940 g / 4-(dimethylamino)pyridine, 1-ethyl-3-((dimethylamino)propyl)carbodiimide hydrochloride / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h 3: 46 percent / RuCl2(=CHPh)(PCy3)2 / CH2Cl2 / 20 h / 25 °C 4: 90 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 0 °C View Scheme

1: 71 percent / borane-dimethyl sulfide; trimethyl borate / tetrahydrofuran / 9 h / 0 - 15 °C 2: 72 percent / imidazole / CH2Cl2 / 3 h / 0 °C View Scheme