diisobutylaluminium hydride in tetrahydrofuran; methanol

1: 90 percent / DIBAL / CH2Cl2 / 1 h / -78 °C 2: 98 percent / benzene / 2 h / Heating 3: 74 percent / diethyl ether; pentane / 1 h / -100 °C 4: 99 percent / imidazole / dimethylformamide / 1) 0 deg C, 45 min, 2) 25 deg C, 2.5 h 5: 95 percent / 4-methylmorpholine N-oxide, OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 1) 0 deg C, 2.5 h, 2) 25 deg C, 12 h 6: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 7: 95 percent / benzene / 3 h / Heating 8: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C 9: 83 percent / Ph3P, CCl4 / 24 h / 100 °C 10: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C 11: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C 12: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 13: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 14: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 15: 82 percent / DIBAL / toluene / 1 h / -78 °C 16: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 17: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C View Scheme

1: 90 percent / DIBAL / CH2Cl2 / 1 h / -78 °C 2: 98 percent / benzene / 2 h / Heating 3: 74 percent / diethyl ether; pentane / 1 h / -100 °C 4: 99 percent / imidazole / dimethylformamide / 1) 0 deg C, 45 min, 2) 25 deg C, 2.5 h 5: 95 percent / 4-methylmorpholine N-oxide, OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 1) 0 deg C, 2.5 h, 2) 25 deg C, 12 h 6: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 7: 95 percent / benzene / 3 h / Heating 8: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C 9: 83 percent / Ph3P, CCl4 / 24 h / 100 °C 10: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C 11: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C 12: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 13: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 14: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 15: 82 percent / DIBAL / toluene / 1 h / -78 °C 16: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 17: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 18: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C 19: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, -78 deg C -> 0 deg C, 30 min 20: 90 percent / NaClO2, isobutylene, NaH2PO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 90 percent / DIBAL / CH2Cl2 / 1 h / -78 °C 2: 98 percent / benzene / 2 h / Heating 3: 74 percent / diethyl ether; pentane / 1 h / -100 °C 4: 99 percent / imidazole / dimethylformamide / 1) 0 deg C, 45 min, 2) 25 deg C, 2.5 h 5: 95 percent / 4-methylmorpholine N-oxide, OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 1) 0 deg C, 2.5 h, 2) 25 deg C, 12 h 6: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 7: 95 percent / benzene / 3 h / Heating 8: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C 9: 83 percent / Ph3P, CCl4 / 24 h / 100 °C 10: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C 11: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C 12: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C 13: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h 14: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C 15: 82 percent / DIBAL / toluene / 1 h / -78 °C 16: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min View Scheme

1: 57 percent / DIBAL-H 2: 89 percent View Scheme

1.1: 70 percent / DIBAL-H / CH2Cl2 / -78 °C 2.1: 90 percent / benzene / Heating 3.1: Bu3P(O); Et2AlCl; (S)-3,3'-(Ph2PO)2-1,1'-binaphthalene-2,2'-diol / CH2Cl2; hexane / 39 h / -40 °C 4.1: TFA / CH2Cl2; hexane / 1 h / 20 °C 5.1: 75 percent / H2SO4 / Heating 6.1: 99 percent / imidazole / dimethylformamide 7.1: 87 percent / DIBAL-H / toluene / -78 °C 8.1: tetrahydrofuran / -78 °C 9.1: tetrahydrofuran 10.1: 51 percent / HCO2NH4; Bu3P / Pd(OAc)2 / benzene / 50 °C 11.1: 89 percent / AcOH; H2O / tetrahydrofuran / 50 °C 12.1: 90 percent / [Ti(O-i-Pr)4]; i-PrMgCl / diethyl ether / -78 - -50 °C 13.1: 65 percent / I2 / CH2Cl2 14.1: 90 percent / NEt3; DMAP / CH2Cl2 15.1: 50 percent / 9-BBN; K3PO4 / [PdCl2(dppf)] / tetrahydrofuran; dimethylformamide; H2O / 60 °C 16.1: 84 percent / NaOH; H2O / methanol 17.1: 2,4,6-trichlorobenzoyl chloride; NEt3 / tetrahydrofuran 17.2: 88 percent / DMAP / toluene; tetrahydrofuran 18.1: 99 percent / HF*pyridine / tetrahydrofuran View Scheme

1: 57 percent / DIBAL-H 2: 89 percent 3: 1) (S)-BINOL-Ti(OiPr)4 View Scheme

N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane 4 h; Irradiation;

N-bromosuccinmide in tetrachloromethane

N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane 36 h;