1: DIBALH / CH2Cl2 / -78 °C 2: K2CO3 / methanol / 20 °C View Scheme

1: With methanol; sodium hydroxide; water T=20°C; 2 h; 2: With hydrogenchloride; water in methanol pH=2;

ammonium hydroxide in methanol T=20°C; 16 h;

1: 65 percent / LiBH4 / ethanol; tetrahydrofuran / 0 - 20 °C 2: thionyl chloride; pyridine / CH2Cl2 / 2 h / -30 - 20 °C View Scheme

1: 57 percent / DIBAL-H 2: 89 percent 3: 80 percent / tetrahydrofuran 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 View Scheme

1.1: DIBAL-H / CH2Cl2 / 5.5 h / -78 °C 2.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C 2.2: 87 percent / tetrahydrofuran / -78 - 20 °C 3.1: SmI2 / tetrahydrofuran / 0.33 h / 0 °C 4.1: 114 mg / H2O; B(OH)3 / tetrahydrofuran / 0.5 h / 20 °C 5.1: 91 percent / Et3B; NaBH4 / methanol; tetrahydrofuran / 17 h / -78 °C 6.1: SOCl2; Et3N / CH2Cl2 / 0.33 h / 0 °C 7.1: 58 mg / Bu4NF*3H2O / tetrahydrofuran / 6 h / Heating 8.1: 79 percent / Et3N; DMAP / CH2Cl2 / 15 h / 20 °C 9.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 10.1: 4.4 mg / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C 11.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C 12.1: 91 percent / pyridine / CH2Cl2 / 2 h / 0 °C 13.1: NMO; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 18 h / 20 °C 14.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C 15.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C 16.1: 63.2 mg / NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C 17.1: 2,4,6-trichlorobenzoyl chloride; Et3N 17.2: 74 percent / 4-dimethylaminopyridine 18.1: 82 percent / Zn; NH4Cl / methanol / 0.08 h / 20 °C 19.1: 38 percent / HF*pyridine / pyridine / 168 h / 35 - 40 °C View Scheme

1.1: 84 percent / LiAlH4 / diethyl ether / 3 h / -78 °C 2.1: 85 percent / Ph3P; CBr4 / CCl4 / 3 h / 20 °C 3.1: 86 percent / 3 h / 160 °C 4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 5.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 5.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 6.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 7.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 7.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 8.1: pyridine / CH2Cl2 / 1 h / 0 °C 9.1: CH2Cl2 / 5 h / 20 °C 10.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 11.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 12.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 13.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 14.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C 15.1: 30 percent / m-CPBA / CHCl3 / 5 h / -10 - 0 °C View Scheme

1: 89 percent / aq. NH3 / methanol / 16 h / 20 °C 2: 56 percent / SOCl2; NMM / dimethylformamide / 5 h / 0 - 20 °C 3: 39 percent / NBS / CCl4 / 80 °C 4: NaN3 / dimethylformamide / 20 h / 20 °C 5: 80 percent / Ph3P / tetrahydrofuran; H2O / 20 h / 20 °C View Scheme

1: 89 percent / aq. NH3 / methanol / 16 h / 20 °C 2: 56 percent / SOCl2; NMM / dimethylformamide / 5 h / 0 - 20 °C View Scheme