1.1: sodium hydride; tetrabutylammonium iodide / tetrahydrofuran 2.1: tetrabutylammonium fluoride / tetrahydrofuran 3.1: 99 percent / SO3*pyridine; ethyldiisopropylamine / CH2Cl2; dimethylsulfoxide / 0 °C 4.1: 92 percent / lithium bis(trimethylsilyl)amide; acetic acid / tetrahydrofuran / -78 °C 5.1: 47 percent / Ph3CBF4 / tetrahydrofuran / 20 °C 6.1: 80 percent / (+/-)-camphorsulfonic acid / methanol / 20 °C 7.1: 74 percent / silver(I) oxide / CH2Cl2 / 50 °C 8.1: 97 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -20 - -10 °C 9.1: 80 percent / tert-butyllithium / tetrahydrofuran / -96 - -78 °C 10.1: 83 percent / Zn(BH4)2 / diethyl ether / 2 h / -20 °C 11.1: 93 percent / imidazole / dimethylformamide / 50 °C 12.1: 81 percent / tert-butyllithium; hexamethylphosphoramide / tetrahydrofuran / -78 - -40 °C 13.1: 83 percent / (bis(trifluoroacetoxy)iodo)benzene / tetrahydrofuran; H2O; methanol / 20 °C 14.1: 99 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 24 h / -5 °C 15.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 20 °C / pH 7 16.1: 99 percent / (COCl)2; dimethyl sulfoxide; triethylamine / CH2Cl2 17.1: 82 percent / CrCl2 / tetrahydrofuran / 0 - 20 °C 18.1: N-methylpyrrolidinone; [Pd{P(2-furyl)3}2Cl2]; hexamethyltin / 20 °C 18.2: [Pd{P(2-furyl)3}2Cl2]; N-methylpyrrolidinone / 20 °C 19.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C 20.1: 81 percent / 4-pyrrolidinopyridine / CH2Cl2 21.1: 89 percent / lithium hydroxide / H2O; tetrahydrofuran / 0 °C 22.1: 88 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 23.1: 66 percent / 2,6-lutidine / CH2Cl2 / -20 °C 24.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C 25.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C 26.1: 78 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C 27.1: 80 percent / dimedone / [Pd(PPh3)4] / tetrahydrofuran / 20 °C 28.1: PhI(OAc)2 / acetonitrile; H2O / 0 °C 29.1: 2,9-dimethyl-1,10-phenanthroline; pyridine / CH2Cl2 / 20 °C 30.1: 61 percent / pyridine*HF / tetrahydrofuran / 50 °C View Scheme

1.1: sBuLi; (-)-(MeO)B(isopinocampheyl)2; BF3*OEt2 / tetrahydrofuran / 14 h / -78 °C 1.2: NaOH; H2O2 / H2O / -78 - 20 °C 2.1: sodium carbonate / methanol / 20 °C 3.1: 99 percent / sodium hydride; tetrabutylammonium iodide / dimethylformamide / 20 °C 4.1: N-methylmorpholine N-oxide; OsO4 / acetone; H2O / 20 °C 4.2: Pb(OAc)4 / benzene 5.1: tert-butyllithium / tetrahydrofuran / -96 - -78 °C 6.1: 99 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / -78 °C 7.1: 77 percent / tert-butyllithium; hexamethylphosphoramide / tetrahydrofuran / -78 - -40 °C 8.1: 84 percent / (bis(trifluoroacetoxy)iodo)benzene / tetrahydrofuran; H2O; methanol / 20 °C 9.1: 84 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 24 h / -5 °C 10.1: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 20 °C / pH 7 11.1: 99 percent / (COCl)2; dimethyl sulfoxide; triethylamine / CH2Cl2 12.1: 82 percent / CrCl2 / tetrahydrofuran / 0 - 20 °C 13.1: N-methylpyrrolidinone; [Pd{P(2-furyl)3}2Cl2]; hexamethyltin / 20 °C 13.2: [Pd{P(2-furyl)3}2Cl2]; N-methylpyrrolidinone / 20 °C 14.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C 15.1: 81 percent / 4-pyrrolidinopyridine / CH2Cl2 16.1: 89 percent / lithium hydroxide / H2O; tetrahydrofuran / 0 °C 17.1: 88 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 18.1: 66 percent / 2,6-lutidine / CH2Cl2 / -20 °C 19.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C 20.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C 21.1: 78 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C 22.1: 80 percent / dimedone / [Pd(PPh3)4] / tetrahydrofuran / 20 °C 23.1: PhI(OAc)2 / acetonitrile; H2O / 0 °C 24.1: 2,9-dimethyl-1,10-phenanthroline; pyridine / CH2Cl2 / 20 °C 25.1: 61 percent / pyridine*HF / tetrahydrofuran / 50 °C View Scheme

1.1: 77 percent / tert-butyllithium; hexamethylphosphoramide / tetrahydrofuran / -78 - -40 °C 2.1: 84 percent / (bis(trifluoroacetoxy)iodo)benzene / tetrahydrofuran; H2O; methanol / 20 °C 3.1: 84 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 24 h / -5 °C 4.1: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 20 °C / pH 7 5.1: 99 percent / (COCl)2; dimethyl sulfoxide; triethylamine / CH2Cl2 6.1: 82 percent / CrCl2 / tetrahydrofuran / 0 - 20 °C 7.1: N-methylpyrrolidinone; [Pd{P(2-furyl)3}2Cl2]; hexamethyltin / 20 °C 7.2: [Pd{P(2-furyl)3}2Cl2]; N-methylpyrrolidinone / 20 °C 8.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C 9.1: 81 percent / 4-pyrrolidinopyridine / CH2Cl2 10.1: 89 percent / lithium hydroxide / H2O; tetrahydrofuran / 0 °C 11.1: 88 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 12.1: 66 percent / 2,6-lutidine / CH2Cl2 / -20 °C 13.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C 14.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C 15.1: 78 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C 16.1: 80 percent / dimedone / [Pd(PPh3)4] / tetrahydrofuran / 20 °C 17.1: PhI(OAc)2 / acetonitrile; H2O / 0 °C 18.1: 2,9-dimethyl-1,10-phenanthroline; pyridine / CH2Cl2 / 20 °C 19.1: 61 percent / pyridine*HF / tetrahydrofuran / 50 °C View Scheme

1.1: imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 20 °C 2.1: 99 percent / hydrogen / Pd(OH)2 / ethyl acetate / 20 °C 3.1: 99 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 20 °C 4.1: tetrahydrofuran / -78 °C 4.2: tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH2Cl2; acetonitrile / 20 °C 5.1: 85 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C 6.1: 91 percent / diisobutylaluminum hydride / toluene / -78 °C 7.1: tetrabutylammonium fluoride; acetic acid / H2O; tetrahydrofuran / 20 °C 8.1: tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH2Cl2 9.1: CrCl2 / tetrahydrofuran; dioxane / 0 °C 10.1: N-methylpyrrolidinone; [Pd{P(2-furyl)3}2Cl2]; hexamethyltin / 20 °C 10.2: [Pd{P(2-furyl)3}2Cl2]; N-methylpyrrolidinone / 20 °C 11.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C 12.1: 81 percent / 4-pyrrolidinopyridine / CH2Cl2 13.1: 89 percent / lithium hydroxide / H2O; tetrahydrofuran / 0 °C 14.1: 88 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 15.1: 66 percent / 2,6-lutidine / CH2Cl2 / -20 °C 16.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C 17.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C 18.1: 78 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C 19.1: 80 percent / dimedone / [Pd(PPh3)4] / tetrahydrofuran / 20 °C 20.1: PhI(OAc)2 / acetonitrile; H2O / 0 °C 21.1: 2,9-dimethyl-1,10-phenanthroline; pyridine / CH2Cl2 / 20 °C 22.1: 61 percent / pyridine*HF / tetrahydrofuran / 50 °C View Scheme

1.1: potassium carbonate / methanol 2.1: sodium hydride; tetrabutylammonium iodide / tetrahydrofuran 3.1: tetrabutylammonium fluoride / tetrahydrofuran 4.1: 99 percent / SO3*pyridine; ethyldiisopropylamine / CH2Cl2; dimethylsulfoxide / 0 °C 5.1: 92 percent / lithium bis(trimethylsilyl)amide; acetic acid / tetrahydrofuran / -78 °C 6.1: 47 percent / Ph3CBF4 / tetrahydrofuran / 20 °C 7.1: 80 percent / (+/-)-camphorsulfonic acid / methanol / 20 °C 8.1: 74 percent / silver(I) oxide / CH2Cl2 / 50 °C 9.1: 97 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -20 - -10 °C 10.1: 80 percent / tert-butyllithium / tetrahydrofuran / -96 - -78 °C 11.1: 83 percent / Zn(BH4)2 / diethyl ether / 2 h / -20 °C 12.1: 93 percent / imidazole / dimethylformamide / 50 °C 13.1: 81 percent / tert-butyllithium; hexamethylphosphoramide / tetrahydrofuran / -78 - -40 °C 14.1: 83 percent / (bis(trifluoroacetoxy)iodo)benzene / tetrahydrofuran; H2O; methanol / 20 °C 15.1: 99 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 24 h / -5 °C 16.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 20 °C / pH 7 17.1: 99 percent / (COCl)2; dimethyl sulfoxide; triethylamine / CH2Cl2 18.1: 82 percent / CrCl2 / tetrahydrofuran / 0 - 20 °C 19.1: N-methylpyrrolidinone; [Pd{P(2-furyl)3}2Cl2]; hexamethyltin / 20 °C 19.2: [Pd{P(2-furyl)3}2Cl2]; N-methylpyrrolidinone / 20 °C 20.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C 21.1: 81 percent / 4-pyrrolidinopyridine / CH2Cl2 22.1: 89 percent / lithium hydroxide / H2O; tetrahydrofuran / 0 °C 23.1: 88 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 24.1: 66 percent / 2,6-lutidine / CH2Cl2 / -20 °C 25.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C 26.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C 27.1: 78 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C 28.1: 80 percent / dimedone / [Pd(PPh3)4] / tetrahydrofuran / 20 °C 29.1: PhI(OAc)2 / acetonitrile; H2O / 0 °C 30.1: 2,9-dimethyl-1,10-phenanthroline; pyridine / CH2Cl2 / 20 °C 31.1: 61 percent / pyridine*HF / tetrahydrofuran / 50 °C View Scheme

1.1: 99 percent / SO3*pyridine; ethyldiisopropylamine / CH2Cl2; dimethylsulfoxide / 0 °C 2.1: 92 percent / lithium bis(trimethylsilyl)amide; acetic acid / tetrahydrofuran / -78 °C 3.1: 47 percent / Ph3CBF4 / tetrahydrofuran / 20 °C 4.1: 80 percent / (+/-)-camphorsulfonic acid / methanol / 20 °C 5.1: 74 percent / silver(I) oxide / CH2Cl2 / 50 °C 6.1: 97 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -20 - -10 °C 7.1: 80 percent / tert-butyllithium / tetrahydrofuran / -96 - -78 °C 8.1: 83 percent / Zn(BH4)2 / diethyl ether / 2 h / -20 °C 9.1: 93 percent / imidazole / dimethylformamide / 50 °C 10.1: 81 percent / tert-butyllithium; hexamethylphosphoramide / tetrahydrofuran / -78 - -40 °C 11.1: 83 percent / (bis(trifluoroacetoxy)iodo)benzene / tetrahydrofuran; H2O; methanol / 20 °C 12.1: 99 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 24 h / -5 °C 13.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 20 °C / pH 7 14.1: 99 percent / (COCl)2; dimethyl sulfoxide; triethylamine / CH2Cl2 15.1: 82 percent / CrCl2 / tetrahydrofuran / 0 - 20 °C 16.1: N-methylpyrrolidinone; [Pd{P(2-furyl)3}2Cl2]; hexamethyltin / 20 °C 16.2: [Pd{P(2-furyl)3}2Cl2]; N-methylpyrrolidinone / 20 °C 17.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C 18.1: 81 percent / 4-pyrrolidinopyridine / CH2Cl2 19.1: 89 percent / lithium hydroxide / H2O; tetrahydrofuran / 0 °C 20.1: 88 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 21.1: 66 percent / 2,6-lutidine / CH2Cl2 / -20 °C 22.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C 23.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C 24.1: 78 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C 25.1: 80 percent / dimedone / [Pd(PPh3)4] / tetrahydrofuran / 20 °C 26.1: PhI(OAc)2 / acetonitrile; H2O / 0 °C 27.1: 2,9-dimethyl-1,10-phenanthroline; pyridine / CH2Cl2 / 20 °C 28.1: 61 percent / pyridine*HF / tetrahydrofuran / 50 °C View Scheme

dichloro bis(acetonitrile) palladium(II); N-ethyl-N,N-diisopropylamine in tetrahydrofuran; N,N-dimethyl-formamide T=25°C; 24 h; Yield given;

pyridine hydrogenfluoride in tetrahydrofuran T=45°C; 6 h; Inert atmosphere;

N-ethyl-N,N-diisopropylamine; lt;Pd(CH3CN)Cl2gt; in tetrahydrofuran; N,N-dimethyl-formamide T=25°C; 48 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

pyridine; tetrabutyl ammonium fluoride; pyridine hydrogenfluoride; acetic acid 1.) 0 deg C, 2.) THF, RT; Yield given. Multistep reaction;