silver nitrate in water; acetonitrile T=20°C; 11 h;

1.1: n-BuLi; B(OMe)3 / tetrahydrofuran 1.2: 95 percent / AcOH; H2O2 / 0 - 20 °C 2.1: 97 percent / LiCl; 3 Angstroem molecular sieves / toluene; various solvent(s) / 24 h / 20 °C 3.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 4.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C 5.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C 6.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 7.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 8.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 9.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 10.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 11.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 12.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 13.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 14.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 15.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 16.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 17.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 18.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 19.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 20.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 21.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 22.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 23.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 23.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 23.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 24.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 25.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme

1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 2: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme

1.1: 96 percent / NaH / diethyl ether; dimethylformamide / 0 - 20 °C 2.1: n-BuLi; B(OMe)3 / tetrahydrofuran 2.2: 95 percent / AcOH; H2O2 / 0 - 20 °C 3.1: 97 percent / LiCl; 3 Angstroem molecular sieves / toluene; various solvent(s) / 24 h / 20 °C 4.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 5.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C 6.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C 7.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 8.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 9.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 11.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 12.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 13.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 14.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 15.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 16.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 17.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 18.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 19.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 20.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 21.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 22.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 23.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 24.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 24.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 24.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 25.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 26.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme

1.1: 97 percent / LiCl; 3 Angstroem molecular sieves / toluene; various solvent(s) / 24 h / 20 °C 2.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 3.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C 4.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C 5.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 6.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 7.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 8.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 9.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 10.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 11.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 12.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 13.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 14.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 15.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 16.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 17.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 18.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 19.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 20.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 21.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 22.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 22.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 22.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 23.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 24.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme

1.1: 83 percent / TEA / CH2Cl2 / 0 °C 2.1: 97 percent / Br2; AcOH / CH2Cl2 / 0.5 h / 20 °C 3.1: 96 percent / K2CO3 / acetone / 1 h / Heating 4.1: 97 percent / aq. NaOH / ethanol / 0.5 h / Heating 5.1: 97 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C 6.1: 79 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 60 °C 7.1: CSA / methanol / 1 h / 20 °C 8.1: n-BuLi / diethyl ether; hexane / 0 - 20 °C 8.2: I2 / diethyl ether; hexane / 0 °C 9.1: 314 mg / conc. HCl / tetrahydrofuran / 0.25 h / 20 °C 10.1: 98 percent / K2CO3 / acetonitrile / 0.67 h / Heating 11.1: 93 percent / N,N,N',N'-tetramethylguanidine / CH2Cl2 / 24 h / 20 °C 12.1: H2; Rh[(COD)-(S,S)-Et-DuPHOS]+OTf- / ethyl acetate / 22 h / 50 °C / 25858.1 Torr 13.1: 100 percent / lithium hydroxide / methanol; tetrahydrofuran; H2O / 0 - 20 °C 14.1: 90 percent / methanol / 1 h / Heating 15.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C 16.1: 93 percent / pyridine; DMAP / 30 h / 50 °C 17.1: TFA; anisole / CH2Cl2 / 9 h / 20 °C 18.1: 19.7 g / ethyl acetate / 1 h / Heating 19.1: 91 percent / TEA / CH2Cl2 / 1 h / 0 °C 20.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C 21.1: NaBH4; H2SO4 / ethanol; CH2Cl2 / 0 °C 22.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating 23.1: 83 percent / tris(dibenzylideneacetone)dipalladium(0); tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating 24.1: aq. NaOH / methanol / 2.5 h / Heating 25.1: 106 mg / pyridine; DMAP / CH2Cl2 / 20 °C 26.1: TFA / CH2Cl2 / 4 h / 20 °C 27.1: 2.08 g / NaHCO3 / CH2Cl2; H2O / 0.17 h / 0 °C 28.1: dimethyldioxirane / methanol; acetone / 2 h / 0 °C 29.1: 652 mg / CSA / acetone / 0 - 20 °C 30.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C 31.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C 32.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH2Cl2 / 2.5 h / 40 °C 33.1: 91 percent / K2CO3 / acetonitrile / 1 h / Heating 34.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C 35.1: 73 percent / BF3*OEt2 / CH2Cl2 / 0 °C 36.1: 92 percent / pyridine; DMAP / 20 °C 37.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C 38.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.67 h / 20 °C 39.1: 84 percent / H2 / Pd/C / tetrahydrofuran / 18 h / 20 °C / 760.05 Torr 40.1: 89 percent / i-Pr2NEt / CH2Cl2 / 3 h / Heating 41.1: 99 percent / K2CO3 / methanol / 0.5 h / 20 °C 42.1: 94 percent / WSCD*HCl; DMAP / CH2Cl2 / 0.17 h / 20 °C 43.1: 98 percent / hydrazine / acetonitrile / 1.33 h / 20 °C 44.1: TFA / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 45.1: 18.0 mg / pyridine; DMAP / 0.5 h / 20 °C 46.1: 92 percent / Zn; AcOH / diethyl ether / 2.5 h / 20 °C 47.1: 96 percent / AcOH; sodium cyanoborohydride / methanol / 1 h / 20 °C 48.1: 89 percent / Pd(PPh3)2Cl2; AcOH; n-Bu3SnH / CH2Cl2 / 0.33 h / 20 °C 49.1: 4-formyl-1-methylpyridinium benzenesulfonate / dimethylformamide; CH2Cl2 / 0.25 h / 20 °C 49.2: DBU / dimethylformamide; CH2Cl2 / 0.42 h / 20 °C 49.3: 54 percent / aq. citric acid / C View Scheme

1.1: 97 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C 2.1: 79 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 60 °C 3.1: CSA / methanol / 1 h / 20 °C 4.1: n-BuLi / diethyl ether; hexane / 0 - 20 °C 4.2: I2 / diethyl ether; hexane / 0 °C 5.1: 314 mg / conc. HCl / tetrahydrofuran / 0.25 h / 20 °C 6.1: 98 percent / K2CO3 / acetonitrile / 0.67 h / Heating 7.1: 93 percent / N,N,N',N'-tetramethylguanidine / CH2Cl2 / 24 h / 20 °C 8.1: H2; Rh[(COD)-(S,S)-Et-DuPHOS]+OTf- / ethyl acetate / 22 h / 50 °C / 25858.1 Torr 9.1: 100 percent / lithium hydroxide / methanol; tetrahydrofuran; H2O / 0 - 20 °C 10.1: 90 percent / methanol / 1 h / Heating 11.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C 12.1: 93 percent / pyridine; DMAP / 30 h / 50 °C 13.1: TFA; anisole / CH2Cl2 / 9 h / 20 °C 14.1: 19.7 g / ethyl acetate / 1 h / Heating 15.1: 91 percent / TEA / CH2Cl2 / 1 h / 0 °C 16.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C 17.1: NaBH4; H2SO4 / ethanol; CH2Cl2 / 0 °C 18.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating 19.1: 83 percent / tris(dibenzylideneacetone)dipalladium(0); tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating 20.1: aq. NaOH / methanol / 2.5 h / Heating 21.1: 106 mg / pyridine; DMAP / CH2Cl2 / 20 °C 22.1: TFA / CH2Cl2 / 4 h / 20 °C 23.1: 2.08 g / NaHCO3 / CH2Cl2; H2O / 0.17 h / 0 °C 24.1: dimethyldioxirane / methanol; acetone / 2 h / 0 °C 25.1: 652 mg / CSA / acetone / 0 - 20 °C 26.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C 27.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C 28.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH2Cl2 / 2.5 h / 40 °C 29.1: 91 percent / K2CO3 / acetonitrile / 1 h / Heating 30.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C 31.1: 73 percent / BF3*OEt2 / CH2Cl2 / 0 °C 32.1: 92 percent / pyridine; DMAP / 20 °C 33.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C 34.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.67 h / 20 °C 35.1: 84 percent / H2 / Pd/C / tetrahydrofuran / 18 h / 20 °C / 760.05 Torr 36.1: 89 percent / i-Pr2NEt / CH2Cl2 / 3 h / Heating 37.1: 99 percent / K2CO3 / methanol / 0.5 h / 20 °C 38.1: 94 percent / WSCD*HCl; DMAP / CH2Cl2 / 0.17 h / 20 °C 39.1: 98 percent / hydrazine / acetonitrile / 1.33 h / 20 °C 40.1: TFA / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 41.1: 18.0 mg / pyridine; DMAP / 0.5 h / 20 °C 42.1: 92 percent / Zn; AcOH / diethyl ether / 2.5 h / 20 °C 43.1: 96 percent / AcOH; sodium cyanoborohydride / methanol / 1 h / 20 °C 44.1: 89 percent / Pd(PPh3)2Cl2; AcOH; n-Bu3SnH / CH2Cl2 / 0.33 h / 20 °C 45.1: 4-formyl-1-methylpyridinium benzenesulfonate / dimethylformamide; CH2Cl2 / 0.25 h / 20 °C 45.2: DBU / dimethylformamide; CH2Cl2 / 0.42 h / 20 °C 45.3: 54 percent / aq. citric acid / CH2Cl2; dimethylformamide / 0.67 h / 20 °C 46.1: 96 percent / sodium acetate / ethanol / 5.5 h / 20 °C 47.1: 93 percent / silver nitrate / acetonitrile; H2O / 17 h / 20 °C View Scheme

1.1: 79 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 60 °C 2.1: CSA / methanol / 1 h / 20 °C 3.1: n-BuLi / diethyl ether; hexane / 0 - 20 °C 3.2: I2 / diethyl ether; hexane / 0 °C 4.1: 314 mg / conc. HCl / tetrahydrofuran / 0.25 h / 20 °C 5.1: 98 percent / K2CO3 / acetonitrile / 0.67 h / Heating 6.1: 93 percent / N,N,N',N'-tetramethylguanidine / CH2Cl2 / 24 h / 20 °C 7.1: H2; Rh[(COD)-(S,S)-Et-DuPHOS]+OTf- / ethyl acetate / 22 h / 50 °C / 25858.1 Torr 8.1: 100 percent / lithium hydroxide / methanol; tetrahydrofuran; H2O / 0 - 20 °C 9.1: 90 percent / methanol / 1 h / Heating 10.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C 11.1: 93 percent / pyridine; DMAP / 30 h / 50 °C 12.1: TFA; anisole / CH2Cl2 / 9 h / 20 °C 13.1: 19.7 g / ethyl acetate / 1 h / Heating 14.1: 91 percent / TEA / CH2Cl2 / 1 h / 0 °C 15.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C 16.1: NaBH4; H2SO4 / ethanol; CH2Cl2 / 0 °C 17.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating 18.1: 83 percent / tris(dibenzylideneacetone)dipalladium(0); tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating 19.1: aq. NaOH / methanol / 2.5 h / Heating 20.1: 106 mg / pyridine; DMAP / CH2Cl2 / 20 °C 21.1: TFA / CH2Cl2 / 4 h / 20 °C 22.1: 2.08 g / NaHCO3 / CH2Cl2; H2O / 0.17 h / 0 °C 23.1: dimethyldioxirane / methanol; acetone / 2 h / 0 °C 24.1: 652 mg / CSA / acetone / 0 - 20 °C 25.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C 26.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C 27.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH2Cl2 / 2.5 h / 40 °C 28.1: 91 percent / K2CO3 / acetonitrile / 1 h / Heating 29.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C 30.1: 73 percent / BF3*OEt2 / CH2Cl2 / 0 °C 31.1: 92 percent / pyridine; DMAP / 20 °C 32.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C 33.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.67 h / 20 °C 34.1: 84 percent / H2 / Pd/C / tetrahydrofuran / 18 h / 20 °C / 760.05 Torr 35.1: 89 percent / i-Pr2NEt / CH2Cl2 / 3 h / Heating 36.1: 99 percent / K2CO3 / methanol / 0.5 h / 20 °C 37.1: 94 percent / WSCD*HCl; DMAP / CH2Cl2 / 0.17 h / 20 °C 38.1: 98 percent / hydrazine / acetonitrile / 1.33 h / 20 °C 39.1: TFA / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 40.1: 18.0 mg / pyridine; DMAP / 0.5 h / 20 °C 41.1: 92 percent / Zn; AcOH / diethyl ether / 2.5 h / 20 °C 42.1: 96 percent / AcOH; sodium cyanoborohydride / methanol / 1 h / 20 °C 43.1: 89 percent / Pd(PPh3)2Cl2; AcOH; n-Bu3SnH / CH2Cl2 / 0.33 h / 20 °C 44.1: 4-formyl-1-methylpyridinium benzenesulfonate / dimethylformamide; CH2Cl2 / 0.25 h / 20 °C 44.2: DBU / dimethylformamide; CH2Cl2 / 0.42 h / 20 °C 44.3: 54 percent / aq. citric acid / CH2Cl2; dimethylformamide / 0.67 h / 20 °C 45.1: 96 percent / sodium acetate / ethanol / 5.5 h / 20 °C 46.1: 93 percent / silver nitrate / acetonitrile; H2O / 17 h / 20 °C View Scheme

1.1: 97 percent / Br2; AcOH / CH2Cl2 / 0.5 h / 20 °C 2.1: 96 percent / K2CO3 / acetone / 1 h / Heating 3.1: 97 percent / aq. NaOH / ethanol / 0.5 h / Heating 4.1: 97 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C 5.1: 79 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 60 °C 6.1: CSA / methanol / 1 h / 20 °C 7.1: n-BuLi / diethyl ether; hexane / 0 - 20 °C 7.2: I2 / diethyl ether; hexane / 0 °C 8.1: 314 mg / conc. HCl / tetrahydrofuran / 0.25 h / 20 °C 9.1: 98 percent / K2CO3 / acetonitrile / 0.67 h / Heating 10.1: 93 percent / N,N,N',N'-tetramethylguanidine / CH2Cl2 / 24 h / 20 °C 11.1: H2; Rh[(COD)-(S,S)-Et-DuPHOS]+OTf- / ethyl acetate / 22 h / 50 °C / 25858.1 Torr 12.1: 100 percent / lithium hydroxide / methanol; tetrahydrofuran; H2O / 0 - 20 °C 13.1: 90 percent / methanol / 1 h / Heating 14.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C 15.1: 93 percent / pyridine; DMAP / 30 h / 50 °C 16.1: TFA; anisole / CH2Cl2 / 9 h / 20 °C 17.1: 19.7 g / ethyl acetate / 1 h / Heating 18.1: 91 percent / TEA / CH2Cl2 / 1 h / 0 °C 19.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C 20.1: NaBH4; H2SO4 / ethanol; CH2Cl2 / 0 °C 21.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating 22.1: 83 percent / tris(dibenzylideneacetone)dipalladium(0); tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating 23.1: aq. NaOH / methanol / 2.5 h / Heating 24.1: 106 mg / pyridine; DMAP / CH2Cl2 / 20 °C 25.1: TFA / CH2Cl2 / 4 h / 20 °C 26.1: 2.08 g / NaHCO3 / CH2Cl2; H2O / 0.17 h / 0 °C 27.1: dimethyldioxirane / methanol; acetone / 2 h / 0 °C 28.1: 652 mg / CSA / acetone / 0 - 20 °C 29.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C 30.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C 31.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH2Cl2 / 2.5 h / 40 °C 32.1: 91 percent / K2CO3 / acetonitrile / 1 h / Heating 33.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C 34.1: 73 percent / BF3*OEt2 / CH2Cl2 / 0 °C 35.1: 92 percent / pyridine; DMAP / 20 °C 36.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C 37.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.67 h / 20 °C 38.1: 84 percent / H2 / Pd/C / tetrahydrofuran / 18 h / 20 °C / 760.05 Torr 39.1: 89 percent / i-Pr2NEt / CH2Cl2 / 3 h / Heating 40.1: 99 percent / K2CO3 / methanol / 0.5 h / 20 °C 41.1: 94 percent / WSCD*HCl; DMAP / CH2Cl2 / 0.17 h / 20 °C 42.1: 98 percent / hydrazine / acetonitrile / 1.33 h / 20 °C 43.1: TFA / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 44.1: 18.0 mg / pyridine; DMAP / 0.5 h / 20 °C 45.1: 92 percent / Zn; AcOH / diethyl ether / 2.5 h / 20 °C 46.1: 96 percent / AcOH; sodium cyanoborohydride / methanol / 1 h / 20 °C 47.1: 89 percent / Pd(PPh3)2Cl2; AcOH; n-Bu3SnH / CH2Cl2 / 0.33 h / 20 °C 48.1: 4-formyl-1-methylpyridinium benzenesulfonate / dimethylformamide; CH2Cl2 / 0.25 h / 20 °C 48.2: DBU / dimethylformamide; CH2Cl2 / 0.42 h / 20 °C 48.3: 54 percent / aq. citric acid / CH2Cl2; dimethylformamide / 0.67 h / 2 View Scheme

1.1: 97 percent / aq. NaOH / ethanol / 0.5 h / Heating 2.1: 97 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C 3.1: 79 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 60 °C 4.1: CSA / methanol / 1 h / 20 °C 5.1: n-BuLi / diethyl ether; hexane / 0 - 20 °C 5.2: I2 / diethyl ether; hexane / 0 °C 6.1: 314 mg / conc. HCl / tetrahydrofuran / 0.25 h / 20 °C 7.1: 98 percent / K2CO3 / acetonitrile / 0.67 h / Heating 8.1: 93 percent / N,N,N',N'-tetramethylguanidine / CH2Cl2 / 24 h / 20 °C 9.1: H2; Rh[(COD)-(S,S)-Et-DuPHOS]+OTf- / ethyl acetate / 22 h / 50 °C / 25858.1 Torr 10.1: 100 percent / lithium hydroxide / methanol; tetrahydrofuran; H2O / 0 - 20 °C 11.1: 90 percent / methanol / 1 h / Heating 12.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C 13.1: 93 percent / pyridine; DMAP / 30 h / 50 °C 14.1: TFA; anisole / CH2Cl2 / 9 h / 20 °C 15.1: 19.7 g / ethyl acetate / 1 h / Heating 16.1: 91 percent / TEA / CH2Cl2 / 1 h / 0 °C 17.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C 18.1: NaBH4; H2SO4 / ethanol; CH2Cl2 / 0 °C 19.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating 20.1: 83 percent / tris(dibenzylideneacetone)dipalladium(0); tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating 21.1: aq. NaOH / methanol / 2.5 h / Heating 22.1: 106 mg / pyridine; DMAP / CH2Cl2 / 20 °C 23.1: TFA / CH2Cl2 / 4 h / 20 °C 24.1: 2.08 g / NaHCO3 / CH2Cl2; H2O / 0.17 h / 0 °C 25.1: dimethyldioxirane / methanol; acetone / 2 h / 0 °C 26.1: 652 mg / CSA / acetone / 0 - 20 °C 27.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C 28.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C 29.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH2Cl2 / 2.5 h / 40 °C 30.1: 91 percent / K2CO3 / acetonitrile / 1 h / Heating 31.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C 32.1: 73 percent / BF3*OEt2 / CH2Cl2 / 0 °C 33.1: 92 percent / pyridine; DMAP / 20 °C 34.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C 35.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.67 h / 20 °C 36.1: 84 percent / H2 / Pd/C / tetrahydrofuran / 18 h / 20 °C / 760.05 Torr 37.1: 89 percent / i-Pr2NEt / CH2Cl2 / 3 h / Heating 38.1: 99 percent / K2CO3 / methanol / 0.5 h / 20 °C 39.1: 94 percent / WSCD*HCl; DMAP / CH2Cl2 / 0.17 h / 20 °C 40.1: 98 percent / hydrazine / acetonitrile / 1.33 h / 20 °C 41.1: TFA / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 42.1: 18.0 mg / pyridine; DMAP / 0.5 h / 20 °C 43.1: 92 percent / Zn; AcOH / diethyl ether / 2.5 h / 20 °C 44.1: 96 percent / AcOH; sodium cyanoborohydride / methanol / 1 h / 20 °C 45.1: 89 percent / Pd(PPh3)2Cl2; AcOH; n-Bu3SnH / CH2Cl2 / 0.33 h / 20 °C 46.1: 4-formyl-1-methylpyridinium benzenesulfonate / dimethylformamide; CH2Cl2 / 0.25 h / 20 °C 46.2: DBU / dimethylformamide; CH2Cl2 / 0.42 h / 20 °C 46.3: 54 percent / aq. citric acid / CH2Cl2; dimethylformamide / 0.67 h / 20 °C 47.1: 96 percent / sodium acetate / ethanol / 5.5 h / 20 °C 48.1: 93 percent / silver nitrate / acet View Scheme