1: 17.1 g / LiAlH4 / diethyl ether / 0.25 h / -78 °C 2: 95 percent / 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide, tetrapropylammonium perruthenate / CH2Cl2 / 0.5 h / Ambient temperature 3: 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 4: 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 5: 46 percent / RuCl2(=CHPh)(PCy3)2 / CH2Cl2 / 20 h / 25 °C 6: 90 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 0 °C 7: 62 percent / Na2EDTA, 1,1,1-trifluoroacetone, Oxone, NaHCO3 / acetonitrile; H2O / 0 °C View Scheme

1: 92 percent / TFA / CH2Cl2 / 1 h / 0 °C 2: 56 percent / methyl(trifluoromethyl)dioxirane / acetonitrile / 0 °C View Scheme

1.1: 83 percent / aq. HCl / 5 h / 90 °C 2.1: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C 3.1: 94 percent / DIBAL / toluene / 1 h / -78 °C 4.1: tetrahydrofuran; hexane / 0.67 h / -78 °C 4.2: 79 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 5.1: 51 percent / ammonium formate; tributylphosphine / Pd(OAc)2 / benzene / 24 h / 50 °C 6.1: 26 percent / Ti(O-i-Pr)4; i-PrMgCl / diethyl ether / 1 h / -50 °C 7.1: 59 percent / I2 / CH2Cl2 / 12 h / 20 °C 8.1: 100 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 9.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation 9.2: 50 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C 10.1: 84 percent / aq. NaOH / methanol / 36 h / 50 °C 11.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 11.2: 88 percent / DMAP / toluene; tetrahydrofuran / 1 h 12.1: 99 percent / HF*pyridine / tetrahydrofuran 13.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2 / -35 °C View Scheme

1.1: 99 percent / imidazole / dimethylformamide / 3 h / 20 °C 2.1: 94 percent / DIBAL / toluene / 1 h / -78 °C 3.1: tetrahydrofuran; hexane / 0.67 h / -78 °C 3.2: 79 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 4.1: 51 percent / ammonium formate; tributylphosphine / Pd(OAc)2 / benzene / 24 h / 50 °C 5.1: 26 percent / Ti(O-i-Pr)4; i-PrMgCl / diethyl ether / 1 h / -50 °C 6.1: 59 percent / I2 / CH2Cl2 / 12 h / 20 °C 7.1: 100 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 8.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation 8.2: 50 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C 9.1: 84 percent / aq. NaOH / methanol / 36 h / 50 °C 10.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 10.2: 88 percent / DMAP / toluene; tetrahydrofuran / 1 h 11.1: 99 percent / HF*pyridine / tetrahydrofuran 12.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2 / -35 °C View Scheme

1.1: tetrahydrofuran; hexane / 0.67 h / -78 °C 1.2: 79 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.1: 51 percent / ammonium formate; tributylphosphine / Pd(OAc)2 / benzene / 24 h / 50 °C 3.1: 26 percent / Ti(O-i-Pr)4; i-PrMgCl / diethyl ether / 1 h / -50 °C 4.1: 59 percent / I2 / CH2Cl2 / 12 h / 20 °C 5.1: 100 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 6.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation 6.2: 50 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C 7.1: 84 percent / aq. NaOH / methanol / 36 h / 50 °C 8.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 8.2: 88 percent / DMAP / toluene; tetrahydrofuran / 1 h 9.1: 99 percent / HF*pyridine / tetrahydrofuran 10.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2 / -35 °C View Scheme

1.1: 94 percent / DIBAL / toluene / 1 h / -78 °C 2.1: tetrahydrofuran; hexane / 0.67 h / -78 °C 2.2: 79 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.1: 51 percent / ammonium formate; tributylphosphine / Pd(OAc)2 / benzene / 24 h / 50 °C 4.1: 26 percent / Ti(O-i-Pr)4; i-PrMgCl / diethyl ether / 1 h / -50 °C 5.1: 59 percent / I2 / CH2Cl2 / 12 h / 20 °C 6.1: 100 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 7.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation 7.2: 50 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C 8.1: 84 percent / aq. NaOH / methanol / 36 h / 50 °C 9.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 9.2: 88 percent / DMAP / toluene; tetrahydrofuran / 1 h 10.1: 99 percent / HF*pyridine / tetrahydrofuran 11.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2 / -35 °C View Scheme

1.1: 26 percent / Ti(O-i-Pr)4; i-PrMgCl / diethyl ether / 1 h / -50 °C 2.1: 59 percent / I2 / CH2Cl2 / 12 h / 20 °C 3.1: 100 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 4.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation 4.2: 50 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C 5.1: 84 percent / aq. NaOH / methanol / 36 h / 50 °C 6.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 6.2: 88 percent / DMAP / toluene; tetrahydrofuran / 1 h 7.1: 99 percent / HF*pyridine / tetrahydrofuran 8.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2 / -35 °C View Scheme

1.1: 51 percent / ammonium formate; tributylphosphine / Pd(OAc)2 / benzene / 24 h / 50 °C 2.1: 26 percent / Ti(O-i-Pr)4; i-PrMgCl / diethyl ether / 1 h / -50 °C 3.1: 59 percent / I2 / CH2Cl2 / 12 h / 20 °C 4.1: 100 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 5.1: 9-BBN / tetrahydrofuran / 0.83 h / 28 °C / microwave irradiation 5.2: 50 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 5 h / 60 °C 6.1: 84 percent / aq. NaOH / methanol / 36 h / 50 °C 7.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 7.2: 88 percent / DMAP / toluene; tetrahydrofuran / 1 h 8.1: 99 percent / HF*pyridine / tetrahydrofuran 9.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2 / -35 °C View Scheme

pyridine hydrogenfluoride T=35 - 40°C; 168 h;

1: 95 percent / HF*pyridine / tetrahydrofuran 2: 45 percent / 3,3-dimethyldioxirane View Scheme