1.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 2.1: Dess-Martin reagent / CH2Cl2 / 1 h / 0 °C 3.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C 4.1: O3 / CH2Cl2 / -78 °C 4.2: PPh3 / CH2Cl2 / 15 h / 20 °C 5.1: PCC; 4 Angstroem molecular sieves; AcONa / CH2Cl2 / 2 h / 0 °C 6.1: Dowex 50wX8 / tetrahydrofuran; H2O / 3 h / 20 °C View Scheme

1.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 0 °C 2.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 2.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C 3.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 4.1: Dess-Martin reagent / CH2Cl2 / 1 h / 0 °C 5.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C 6.1: O3 / CH2Cl2 / -78 °C 6.2: PPh3 / CH2Cl2 / 15 h / 20 °C 7.1: PCC; 4 Angstroem molecular sieves; AcONa / CH2Cl2 / 2 h / 0 °C 8.1: Dowex 50wX8 / tetrahydrofuran; H2O / 3 h / 20 °C View Scheme

1.1: DIBAL-H / toluene; hexane / 1 h / -78 °C 2.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 0 °C 3.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 3.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C 4.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 5.1: Dess-Martin reagent / CH2Cl2 / 1 h / 0 °C 6.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C 7.1: O3 / CH2Cl2 / -78 °C 7.2: PPh3 / CH2Cl2 / 15 h / 20 °C 8.1: PCC; 4 Angstroem molecular sieves; AcONa / CH2Cl2 / 2 h / 0 °C 9.1: Dowex 50wX8 / tetrahydrofuran; H2O / 3 h / 20 °C View Scheme

1.1: D-(-)-diethyl tartrate; Ti(O-isoiPr)4; BuOOH / CH2Cl2 / 20 h / -20 °C 2.1: CuCN / tetrahydrofuran; diethyl ether / 1 h / -30 °C 2.2: tetrahydrofuran; diethyl ether / 8 h / -12 °C 3.1: pyridinium p-toluenesulfonate / CHCl3 / 12 h / 20 °C 4.1: O3 / CH2Cl2 / -78 °C 4.2: Ph3P / CH2Cl2 / 12 h / 20 °C 5.1: benzene / 7 h / 65 °C 6.1: DIBAL-H / toluene; hexane / 1 h / -78 °C 7.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 0 °C 8.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 8.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C 9.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 10.1: Dess-Martin reagent / CH2Cl2 / 1 h / 0 °C 11.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C 12.1: O3 / CH2Cl2 / -78 °C 12.2: PPh3 / CH2Cl2 / 15 h / 20 °C 13.1: PCC; 4 Angstroem molecular sieves; AcONa / CH2Cl2 / 2 h / 0 °C 14.1: Dowex 50wX8 / tetrahydrofuran; H2O / 3 h / 20 °C View Scheme

1: PCC; 4 Angstroem molecular sieves; AcONa / CH2Cl2 / 2 h / 0 °C 2: Dowex 50wX8 / tetrahydrofuran; H2O / 3 h / 20 °C View Scheme

1: 84 percent / H2SO4 / methanol / 14 h / Heating 2: 85 percent / K2CO3 / CH2Cl2; methanol / 3 h / Ambient temperature View Scheme

1: 59 percent / H2SO4 / methanol / 14 h / Heating 2: 85 percent / K2CO3 / CH2Cl2; methanol / 3 h / Ambient temperature View Scheme

1: 70 percent / tetrahydrofuran / 1.5 h / -78 - 0 °C 2: 0.95 g / 30percent H2O2, 30 percent KOH / ethanol / 1.) 45 deg C, 1 h, 2.) reflux, 6 h 3: 91 percent / HCL / 0.67 h 4: 80 percent / pyridine / 1 h / 0 °C 5: 94 percent / 5percent NaOH / tetrahydrofuran / 24 h / 0 °C 6: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h 7: 6.2 g / sodium / methanol / 0.5 h / 0 °C View Scheme

1: 91 percent / HCL / 0.67 h 2: 80 percent / pyridine / 1 h / 0 °C 3: 94 percent / 5percent NaOH / tetrahydrofuran / 24 h / 0 °C 4: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h 5: 6.2 g / sodium / methanol / 0.5 h / 0 °C View Scheme

1: 94 percent / 5percent NaOH / tetrahydrofuran / 24 h / 0 °C 2: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h 3: 6.2 g / sodium / methanol / 0.5 h / 0 °C View Scheme