1.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C 2.1: PCC; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C 3.1: NaH / tetrahydrofuran / 0.08 h / 20 °C 3.2: tetrahydrofuran / 1 h 4.1: LiAlH4; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C 5.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C 6.1: 1.0 M aq. NaOH / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme

1: HCl View Scheme

tetrabutyl ammonium fluoride in tetrahydrofuran 48 h; Yield given;

1: Ti(Oi-Pr)4, (-)-diethyl tartrate, t-BuOOH, 4 Angstroem molecular sieves / CH2Cl2 / -20 °C 2: 70 percent / CuCN / diethyl ether; tetrahydrofuran / -12 °C 3: 88 percent / PPTS / Ambient temperature 4: O3 / CH2Cl2 / -78 °C 5: benzene / 65 °C 6: 95 percent / DIBAL-H / toluene / -78 °C 7: PCC, 4 Angstroem molecular sieves, NaOAc / CH2Cl2 / 0 °C 8: n-BuLi / tetrahydrofuran / -78 - 0 °C 9: TBAF / tetrahydrofuran / Ambient temperature 10: Dess-Martin reagent / CH2Cl2 / 0 °C 11: 93 percent / Ni(acac)2, PPh3, DIBAL-H, 1,3-cyclohexadiene / toluene / 1 h / Ambient temperature 12: imidazole / dimethylformamide 13: O3 / CH2Cl2 / -78 °C 14: t-BuOK / tetrahydrofuran / Ambient temperature 16: TBAF / tetrahydrofuran 17: 95 percent / pyridine; CH2Cl2 / Ambient temperature 18: DOWEX 50WX8 / methanol / 50 °C 19: Et3N / CH2Cl2 20: PPTS / CH2Cl2 / Ambient temperature 21: TBAF / tetrahydrofuran / Ambient temperature 22: PCC, 4 Angstroem molecular sieves, NaOAc / CH2Cl2 / 0 °C 23: NaH / tetrahydrofuran / Ambient temperature 24: 92 percent / (S)-binaphthol, LiAlH4 / ethanol; tetrahydrofuran / -100 - -78 °C 25: 93 percent / acetic acid / H2O; tetrahydrofuran / 40 °C 26: 95 percent / 1N NaOH / methanol; tetrahydrofuran / Ambient temperature View Scheme

1: MsCl, DMAP 3: 97 percent / PPTS / methanol 4: CrO3, H2SO4 5: L-selectride 6: 75 percent / Na, liq. NH3 View Scheme

2: 97 percent / PPTS / methanol 3: CrO3, H2SO4 4: L-selectride 5: 75 percent / Na, liq. NH3 View Scheme

1: pyridine / 48 h / -18 °C 2: 1) t-BuOK / 1) DMSO, RT, 2) DMSO, 30 min 3: DIBAL / toluene; CH2Cl2 / 0.5 h / -78 °C 4: BF3*Et2O / 2 h / -20 °C 5: imidazole / dimethylformamide / 0.17 h / 40 °C 6: 80percent m-chloroperbenzoic acid / CH2Cl2 / 1) -78 to 0 deg C, 30 min,2) 0 deg C,2 h 7: 1) n-butyllithium, 2) BF3*Et2O / 1) THF, hexane, -78 deg C, 5 min,2) THF, hexane, 10 min, 3) THF, hexane, -30 deg C, 2 h 8: pyridine / 15 h / Ambient temperature 9: 6percent sodium amalgam / tetrahydrofuran; methanol / 3 h / Ambient temperature 10: 77 percent / 0.3N hydrochloric acid / acetonitrile / 2 h 11: 1) t-BuOK / 1) THF, 2) THF, 30 min 12: tetrabutylammonium fluoride / tetrahydrofuran / 48 h View Scheme

1: 1) t-BuOK / 1) THF, 2) THF, 30 min 2: tetrabutylammonium fluoride / tetrahydrofuran / 48 h View Scheme

1: 77 percent / 0.3N hydrochloric acid / acetonitrile / 2 h 2: 1) t-BuOK / 1) THF, 2) THF, 30 min 3: tetrabutylammonium fluoride / tetrahydrofuran / 48 h View Scheme

1: pyridine / 15 h / Ambient temperature 2: 6percent sodium amalgam / tetrahydrofuran; methanol / 3 h / Ambient temperature 3: 77 percent / 0.3N hydrochloric acid / acetonitrile / 2 h 4: 1) t-BuOK / 1) THF, 2) THF, 30 min 5: tetrabutylammonium fluoride / tetrahydrofuran / 48 h View Scheme