1.1: 60 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / toluene / 15 h / 20 °C 2.1: NaOH / tetrahydrofuran; H2O / 12 h / 20 °C 2.2: NaOH / dioxane; H2O / 12 h / 20 °C View Scheme

1: kinetic resolution through transesterification using acylase I from Aspergillus sp. and vinyl butyrate 2: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 90 min, 2.) CH2Cl2, from -70 deg C to RT 3: 70 percent / KMnO4, MgSO4 / acetone / 0.5 h / Ambient temperature View Scheme

1: 95 percent / 1 M aq.K2CO3 / tetrahydrofuran / Ambient temperature 2: kinetic resolution through transesterification using acylase I from Aspergillus sp. and vinyl butyrate 3: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 90 min, 2.) CH2Cl2, from -70 deg C to RT 4: 70 percent / KMnO4, MgSO4 / acetone / 0.5 h / Ambient temperature View Scheme

multistep reaction; var. α,ω-chlorobromoalkane; Product distribution;

1.1: 84 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 24 h / -5 °C 2.1: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 20 °C / pH 7 3.1: 99 percent / (COCl)2; dimethyl sulfoxide; triethylamine / CH2Cl2 4.1: 82 percent / CrCl2 / tetrahydrofuran / 0 - 20 °C 5.1: N-methylpyrrolidinone; [Pd{P(2-furyl)3}2Cl2]; hexamethyltin / 20 °C 5.2: [Pd{P(2-furyl)3}2Cl2]; N-methylpyrrolidinone / 20 °C 6.1: 81 percent / LiAlH(OtBu)3 / tetrahydrofuran / -10 °C 7.1: 81 percent / 4-pyrrolidinopyridine / CH2Cl2 8.1: 89 percent / lithium hydroxide / H2O; tetrahydrofuran / 0 °C 9.1: 88 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 10.1: 66 percent / 2,6-lutidine / CH2Cl2 / -20 °C 11.1: 88 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C 12.1: 81 percent / potassium carbonate / dimethylformamide / 20 °C 13.1: 78 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / -78 - -20 °C 14.1: 80 percent / dimedone / [Pd(PPh3)4] / tetrahydrofuran / 20 °C 15.1: PhI(OAc)2 / acetonitrile; H2O / 0 °C 16.1: 2,9-dimethyl-1,10-phenanthroline; pyridine / CH2Cl2 / 20 °C 17.1: 61 percent / pyridine*HF / tetrahydrofuran / 50 °C View Scheme

1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 1 h / -15 °C / |Inert atmosphere 1.2: 16 h / |Inert atmosphere 2.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 18 h / 0 - 20 °C / |Inert atmosphere View Scheme

1: 1) N-methylmorpholine, isobutyl chloroformate / 1) THF, 0 deg C to 5 deg C, 2) THF, r.t. 2: HCl / CH2Cl2 / 0 - 5 °C View Scheme

benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ammonia in DMF (N,N-dimethyl-formamide) 5 h;

ammonium hydroxide; triethylamine in tetrahydrofuran

boron trifluoride diethyl etherate