1.1: Dess-Martin reagent / CH2Cl2 / 2 h / 0 °C 2.1: 54 percent / Ni(cod)2; PPh3; 1,3-cyclohexadiene / iBu2-ALAC / tetrahydrofuran / 6 h / 25 °C 3.1: DMAP; pyridine / CH2Cl2 / 2 h / 20 °C 4.1: Dowex50W / methanol / 0.5 h / 50 °C 5.1: Et3N; DMAP / CH2Cl2 / 36 h / 20 °C 6.1: pyridinium p-toluenesulfonate / CH2Cl2 / 12 h / 20 °C 7.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C 8.1: PCC; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C 9.1: NaH / tetrahydrofuran / 0.08 h / 20 °C 9.2: tetrahydrofuran / 1 h 10.1: LiAlH4; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C 11.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C 12.1: 1.0 M aq. NaOH / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme

1: Dess-Martin reagent / CH2Cl2 / 0 °C 2: 53 percent / Ni(acac)2, PPh3, DIBAL-H, 1,3-cyclohexadiene / tetrahydrofuran / 15 h / Ambient temperature 3: 95 percent / pyridine; CH2Cl2 / Ambient temperature 4: DOWEX 50WX8 / methanol / 50 °C 5: Et3N / CH2Cl2 6: PPTS / CH2Cl2 / Ambient temperature 7: TBAF / tetrahydrofuran / Ambient temperature 8: PCC, 4 Angstroem molecular sieves, NaOAc / CH2Cl2 / 0 °C 9: NaH / tetrahydrofuran / Ambient temperature 10: 92 percent / (S)-binaphthol, LiAlH4 / ethanol; tetrahydrofuran / -100 - -78 °C 11: 93 percent / acetic acid / H2O; tetrahydrofuran / 40 °C 12: 95 percent / 1N NaOH / methanol; tetrahydrofuran / Ambient temperature View Scheme