tetrabutyl ammonium fluoride in tetrahydrofuran T=0°C; 8 h;

1: NaClO2; 2-methyl-2-butene; NaH2PO4*2H2O / H2O; 2-methyl-propan-2-ol / 1 h / cooling 2: H2 / Pd(OH)2/C / ethanol / 4 h / 20 °C 3: toluene / 1 h / Heating 4: DIBAL-H / CH2Cl2; toluene / 1 h / 0 °C 5: aq. K2CO3 / tetrahydrofuran / 2 h / 0 °C 6: (n-Bu)4NF / tetrahydrofuran / 8 h / 0 °C View Scheme

1: H2 / Pd(OH)2/C / ethanol / 4 h / 20 °C 2: toluene / 1 h / Heating 3: DIBAL-H / CH2Cl2; toluene / 1 h / 0 °C 4: aq. K2CO3 / tetrahydrofuran / 2 h / 0 °C 5: (n-Bu)4NF / tetrahydrofuran / 8 h / 0 °C View Scheme

1: formic acid / diethyl ether / 1 h / 0 °C 2: pyridinium chlorochromate; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 15 h / 20 °C 3: NaClO2; 2-methyl-2-butene; NaH2PO4*2H2O / H2O; 2-methyl-propan-2-ol / 1 h / cooling 4: H2 / Pd(OH)2/C / ethanol / 4 h / 20 °C 5: toluene / 1 h / Heating 6: DIBAL-H / CH2Cl2; toluene / 1 h / 0 °C 7: aq. K2CO3 / tetrahydrofuran / 2 h / 0 °C 8: (n-Bu)4NF / tetrahydrofuran / 8 h / 0 °C View Scheme

1: pyridinium chlorochromate; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 15 h / 20 °C 2: NaClO2; 2-methyl-2-butene; NaH2PO4*2H2O / H2O; 2-methyl-propan-2-ol / 1 h / cooling 3: H2 / Pd(OH)2/C / ethanol / 4 h / 20 °C 4: toluene / 1 h / Heating 5: DIBAL-H / CH2Cl2; toluene / 1 h / 0 °C 6: aq. K2CO3 / tetrahydrofuran / 2 h / 0 °C 7: (n-Bu)4NF / tetrahydrofuran / 8 h / 0 °C View Scheme

1: triethylamine / CH2Cl2 / 0 - 20 °C 2: NaN3 / dimethylformamide / 1 h / 100 °C 3: formic acid / diethyl ether / 1 h / 0 °C 4: pyridinium chlorochromate; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 15 h / 20 °C 5: NaClO2; 2-methyl-2-butene; NaH2PO4*2H2O / H2O; 2-methyl-propan-2-ol / 1 h / cooling 6: H2 / Pd(OH)2/C / ethanol / 4 h / 20 °C 7: toluene / 1 h / Heating 8: DIBAL-H / CH2Cl2; toluene / 1 h / 0 °C 9: aq. K2CO3 / tetrahydrofuran / 2 h / 0 °C 10: (n-Bu)4NF / tetrahydrofuran / 8 h / 0 °C View Scheme

1: 97 percent / Na2CO3 / methanol / 4 h / 20 °C View Scheme

1: ethanol / Resolution of racemate; Cooling 2: triethylamine / dichloromethane / 20 °C View Scheme

1.1: Et3N / tetrahydrofuran; diethyl ether / 1 h / 0 °C 2.1: diethyl ether / 3 h / 0 °C 2.2: AgOBz; Et3N / 3 h / 0 - 20 °C 3.1: LiAlH4 / diethyl ether / 0.5 h / 0 °C View Scheme

1: DIBAL-H / CH2Cl2; toluene / 1 h / 0 °C 2: aq. K2CO3 / tetrahydrofuran / 2 h / 0 °C 3: (n-Bu)4NF / tetrahydrofuran / 8 h / 0 °C View Scheme