1: H2SO4 2: H2O / ethanol / 3 h / 80 °C View Scheme

potassium carbonate in methanol T=20°C;

1: 40 percent / CHCl3 / Ambient temperature 2: 90 percent / sodium acetate / ethanol; H2O / Ambient temperature 3: 50 percent / SeO2 / acetic acid / 0.25 h / Heating 4: 50 percent / 0.08 h / 145 °C View Scheme

1: 89 percent 2: 80 percent / tetrahydrofuran View Scheme

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

1.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C 1.2: 87 percent / tetrahydrofuran / -78 - 20 °C 2.1: SmI2 / tetrahydrofuran / 0.33 h / 0 °C 3.1: 114 mg / H2O; B(OH)3 / tetrahydrofuran / 0.5 h / 20 °C 4.1: 91 percent / Et3B; NaBH4 / methanol; tetrahydrofuran / 17 h / -78 °C 5.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 6.1: 58 mg / Bu4NF*3H2O / tetrahydrofuran / 6 h / Heating 7.1: 79 percent / Et3N; DMAP / CH2Cl2 / 15 h / 20 °C 8.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 9.1: 4.4 mg / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 10.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 11.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 12.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 13.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 14.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 15.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 16.1: 2,4,6-trichlorobenzoyl chloride; Et3N 16.2: 74 percent / 4-dimethylaminopyridine 17.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 18.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 83 percent / benzene / Heating 2.1: 60 percent / (S)-(-)-1,1'-bi-2-naphthol; Ti(O-i-Pr)4; 4 Angstroem sieves / CH2Cl2 / 70 h / -78 - -20 °C 3.1: 96 percent / 4-DMAP; Et3N / CH2Cl2 / 2 h 4.1: N-methylmorpholine N-oxide; water / OsO4 / acetone; butan-1-ol / 2 h / 0 °C 5.1: NaIO4 / tetrahydrofuran; H2O / 1.25 h / 20 °C 6.1: 0.141 g / tetrahydrofuran; hexane / 0.67 h / -20 °C 7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / 20 °C 7.2: 77 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 3 h / 20 °C 8.1: 71 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 9.1: 0.055 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 11.1: 0.052 g / NaBH4 / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 12.1: 94 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 13.1: 92 percent / HF*pyridine / tetrahydrofuran / 2 h / 0 - 20 °C 14.1: 97 percent / 3,3-dimethyldioxirane / CH2Cl2; acetone / 2.5 h / -78 - -50 °C View Scheme

1.1: 83 percent / benzene / Heating 2.1: 60 percent / (S)-(-)-1,1'-bi-2-naphthol; Ti(O-i-Pr)4; 4 Angstroem sieves / CH2Cl2 / 70 h / -78 - -20 °C 3.1: 96 percent / 4-DMAP; Et3N / CH2Cl2 / 2 h 4.1: N-methylmorpholine N-oxide; water / OsO4 / acetone; butan-1-ol / 2 h / 0 °C 5.1: NaIO4 / tetrahydrofuran; H2O / 1.25 h / 20 °C 6.1: 0.141 g / tetrahydrofuran; hexane / 0.67 h / -20 °C 7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / 20 °C 7.2: 77 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 3 h / 20 °C 8.1: 71 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 9.1: 0.055 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 11.1: 0.052 g / NaBH4 / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 12.1: 94 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 13.1: 92 percent / HF*pyridine / tetrahydrofuran / 2 h / 0 - 20 °C View Scheme

in chloroform Ambient temperature;

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