1.1: 810 mg / NaHCO3; Dess-Martin periodinane / CH2Cl2 / 1.5 h / 20 °C 2.1: triethylamine / dimethylformamide / 43 h / 130 °C 3.1: 567 mg / dimethyldioxirane / CH2Cl2 / -78 - 20 °C 4.1: 92 percent / diisopropylethylamine; 4-N,N-dimethylaminopyridine / CH2Cl2 / 24 h / 20 °C 5.1: LiHMDS / tetrahydrofuran / 2 h / -13 - -12 °C 5.2: tetrahydrofuran / 0.5 h / -95 - -90 °C 6.1: ozone; oxygen / CH2Cl2 / -78 °C 7.1: 153 mg / diisopropylamine / CH2Cl2 / -78 - 20 °C 8.1: zinc borohydride / diethyl ether / 0.5 h / -29 °C 8.2: 80 percent / tetrabutylammonium fluoride / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C 9.1: 52 percent / NaHCO3 / toluene / 42 h / 80 °C 10.1: 84 percent / K2CO3; MgBr2*Et2O; n-butanethiol / diethyl ether / 0.5 h / 20 °C 11.1: 86 percent / 4-N,N-dimethylaminopyridine / CH2Cl2 / 1 h / 20 °C 12.1: 100 percent / p-toluenesulfonic acid monohydrate / 1.75 h / 20 °C 13.1: 83 percent / aq. HCl / methanol / 0.75 h / 45 °C 14.1: 91 percent / CH2Cl2 / 1.25 h / 20 °C View Scheme

1: 810 mg / NaHCO3; Dess-Martin periodinane / CH2Cl2 / 1.5 h / 20 °C 2: triethylamine / dimethylformamide / 43 h / 130 °C 3: 567 mg / dimethyldioxirane / CH2Cl2 / -78 - 20 °C 4: 90 percent / triethylamine / dimethylformamide / 48 h / 125 °C 5: 94 percent / phenylselenium bromide / CH2Cl2 / 2 h / 0 - 10 °C 6: 86 percent / sodium borohydride / methanol / 1 h / 0 °C 7: 19 mg / toluene / 4 h / 80 °C 8: 98 percent / tetrabutylammoonium fluoride / tetrahydrofuran / 3 h / 20 °C 9: 68 percent / polymer supported para-toluenesulfonic acid; 4 Angstroem molecular sieves / CH2Cl2 / 16 h / 20 °C 10: aq. HCl / methanol / 2 h / 40 °C 11: 3 mg / 4-N,N-dimethylaminopyridine / CH2Cl2 / 1 h / 20 °C View Scheme