1.1: CuCN / tetrahydrofuran; diethyl ether / 1 h / -30 °C 1.2: tetrahydrofuran; diethyl ether / 8 h / -12 °C 2.1: pyridinium p-toluenesulfonate / CHCl3 / 12 h / 20 °C 3.1: O3 / CH2Cl2 / -78 °C 3.2: Ph3P / CH2Cl2 / 12 h / 20 °C 4.1: benzene / 7 h / 65 °C 5.1: DIBAL-H / toluene; hexane / 1 h / -78 °C 6.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 0 °C 7.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 7.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C 8.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 9.1: Dess-Martin reagent / CH2Cl2 / 1 h / 0 °C 10.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C 11.1: O3 / CH2Cl2 / -78 °C 11.2: PPh3 / CH2Cl2 / 15 h / 20 °C 12.1: PCC; 4 Angstroem molecular sieves; AcONa / CH2Cl2 / 2 h / 0 °C 13.1: Dowex 50wX8 / tetrahydrofuran; H2O / 3 h / 20 °C View Scheme

1.1: CuCN / tetrahydrofuran; diethyl ether / 1 h / -30 °C 1.2: tetrahydrofuran; diethyl ether / 8 h / -12 °C 2.1: pyridinium p-toluenesulfonate / CHCl3 / 12 h / 20 °C 3.1: O3 / CH2Cl2 / -78 °C 3.2: Ph3P / CH2Cl2 / 12 h / 20 °C 4.1: benzene / 7 h / 65 °C 5.1: DIBAL-H / toluene; hexane / 1 h / -78 °C 6.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 0 °C 7.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 7.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C 8.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 9.1: Dess-Martin reagent / CH2Cl2 / 1 h / 0 °C 10.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C 11.1: imidazole / dimethylformamide / 7 h / 20 °C 12.1: O3; O2 / CH2Cl2 / -78 °C 12.2: PPh3 / CH2Cl2 / 12 h / 20 °C 13.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 13.2: tetrahydrofuran / 0.25 h 14.1: methanol; diethyl ether / 0 °C 15.1: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 16.1: DMAP; pyridine / CH2Cl2 / 2 h / 20 °C 17.1: Dowex50W / methanol / 0.5 h / 50 °C 18.1: Et3N; DMAP / CH2Cl2 / 36 h / 20 °C 19.1: pyridinium p-toluenesulfonate / CH2Cl2 / 12 h / 20 °C 20.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C 21.1: PCC; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C 22.1: NaH / tetrahydrofuran / 0.08 h / 20 °C 22.2: tetrahydrofuran / 1 h 23.1: LiAlH4; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C 24.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C 25.1: 1.0 M aq. NaOH / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme

1: 70 percent / CuCN / diethyl ether; tetrahydrofuran / -12 °C 2: 88 percent / PPTS / Ambient temperature 3: O3 / CH2Cl2 / -78 °C 4: benzene / 65 °C 5: 95 percent / DIBAL-H / toluene / -78 °C 6: PCC, 4 Angstroem molecular sieves, NaOAc / CH2Cl2 / 0 °C 7: n-BuLi / tetrahydrofuran / -78 - 0 °C 8: TBAF / tetrahydrofuran / Ambient temperature 9: Dess-Martin reagent / CH2Cl2 / 0 °C 10: 93 percent / Ni(acac)2, PPh3, DIBAL-H, 1,3-cyclohexadiene / toluene / 1 h / Ambient temperature 11: imidazole / dimethylformamide 12: O3 / CH2Cl2 / -78 °C 13: t-BuOK / tetrahydrofuran / Ambient temperature 15: TBAF / tetrahydrofuran 16: 95 percent / pyridine; CH2Cl2 / Ambient temperature 17: DOWEX 50WX8 / methanol / 50 °C 18: Et3N / CH2Cl2 19: PPTS / CH2Cl2 / Ambient temperature 20: TBAF / tetrahydrofuran / Ambient temperature 21: PCC, 4 Angstroem molecular sieves, NaOAc / CH2Cl2 / 0 °C 22: NaH / tetrahydrofuran / Ambient temperature 23: 92 percent / (S)-binaphthol, LiAlH4 / ethanol; tetrahydrofuran / -100 - -78 °C 24: 93 percent / acetic acid / H2O; tetrahydrofuran / 40 °C 25: 95 percent / 1N NaOH / methanol; tetrahydrofuran / Ambient temperature View Scheme

1.1: CuCN / tetrahydrofuran; diethyl ether / 1 h / -30 °C 1.2: tetrahydrofuran; diethyl ether / 8 h / -12 °C 2.1: pyridinium p-toluenesulfonate / CHCl3 / 12 h / 20 °C 3.1: O3 / CH2Cl2 / -78 °C 3.2: Ph3P / CH2Cl2 / 12 h / 20 °C 4.1: benzene / 7 h / 65 °C 5.1: DIBAL-H / toluene; hexane / 1 h / -78 °C 6.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 0 °C 7.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 7.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C 8.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 9.1: Dess-Martin reagent / CH2Cl2 / 1 h / 0 °C 10.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C 11.1: O3 / CH2Cl2 / -78 °C 11.2: PPh3 / CH2Cl2 / 15 h / 20 °C 12.1: PCC; 4 Angstroem molecular sieves; AcONa / CH2Cl2 / 2 h / 0 °C 13.1: Dowex 50wX8 / tetrahydrofuran; H2O / 3 h / 20 °C 14.1: imidazole / dimethylformamide / 2 h / 0 °C View Scheme