1.1: O3 / CH2Cl2 / -78 °C 1.2: Ph3P / CH2Cl2 / 12 h / 20 °C 2.1: benzene / 7 h / 65 °C 3.1: DIBAL-H / toluene; hexane / 1 h / -78 °C 4.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 0 °C 5.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 5.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C 6.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 7.1: Dess-Martin reagent / CH2Cl2 / 1 h / 0 °C 8.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C 9.1: imidazole / dimethylformamide / 7 h / 20 °C 10.1: O3; O2 / CH2Cl2 / -78 °C 10.2: PPh3 / CH2Cl2 / 12 h / 20 °C 11.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 11.2: tetrahydrofuran / 0.25 h 12.1: methanol; diethyl ether / 0 °C 13.1: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 14.1: DMAP; pyridine / CH2Cl2 / 2 h / 20 °C 15.1: Dowex50W / methanol / 0.5 h / 50 °C 16.1: Et3N; DMAP / CH2Cl2 / 36 h / 20 °C 17.1: pyridinium p-toluenesulfonate / CH2Cl2 / 12 h / 20 °C 18.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C 19.1: PCC; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C 20.1: NaH / tetrahydrofuran / 0.08 h / 20 °C 20.2: tetrahydrofuran / 1 h 21.1: LiAlH4; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C 22.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C 23.1: 1.0 M aq. NaOH / methanol; tetrahydrofuran / 2 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: imidazole / dimethylformamide / 7 h / 20 °C 7.1: O3; O2 / CH2Cl2 / -78 °C 7.2: PPh3 / CH2Cl2 / 12 h / 20 °C 8.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 8.2: tetrahydrofuran / 0.25 h 9.1: methanol; diethyl ether / 0 °C 10.1: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 11.1: DMAP; pyridine / CH2Cl2 / 2 h / 20 °C 12.1: Dowex50W / methanol / 0.5 h / 50 °C 13.1: Et3N; DMAP / CH2Cl2 / 36 h / 20 °C 14.1: pyridinium p-toluenesulfonate / CH2Cl2 / 12 h / 20 °C 15.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C 16.1: PCC; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C 17.1: NaH / tetrahydrofuran / 0.08 h / 20 °C 17.2: tetrahydrofuran / 1 h 18.1: LiAlH4; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C 19.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C 20.1: 1.0 M aq. NaOH / methanol; tetrahydrofuran / 2 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: imidazole / dimethylformamide / 7 h / 20 °C 8.1: O3; O2 / CH2Cl2 / -78 °C 8.2: PPh3 / CH2Cl2 / 12 h / 20 °C 9.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C 9.2: tetrahydrofuran / 0.25 h 10.1: methanol; diethyl ether / 0 °C 11.1: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 12.1: DMAP; pyridine / CH2Cl2 / 2 h / 20 °C 13.1: Dowex50W / methanol / 0.5 h / 50 °C 14.1: Et3N; DMAP / CH2Cl2 / 36 h / 20 °C 15.1: pyridinium p-toluenesulfonate / CH2Cl2 / 12 h / 20 °C 16.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C 17.1: PCC; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C 18.1: NaH / tetrahydrofuran / 0.08 h / 20 °C 18.2: tetrahydrofuran / 1 h 19.1: LiAlH4; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C 20.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C 21.1: 1.0 M aq. NaOH / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme

1: 95 percent / DMAP; Et3N / CH2Cl2 2: K2CO3 / methanol 3: imidazole / dimethylformamide 4: Et2AlCl / CH2Cl2 / 2 h / -50 °C 5: Dess-Martin periodinane; NaHCO3 / CH2Cl2 6: KOtBu / tetrahydrofuran 7: 84 percent / Grubbs' 2nd generation catalyst / CH2Cl2 / 12 h / 40 °C 8: DIBAL-H / CH2Cl2 / -78 °C 9: KOtBu / tetrahydrofuran 10: HCl / tetrahydrofuran / 48 h View Scheme

1.1: 54 percent / Ni(cod)2; PPh3; 1,3-cyclohexadiene / iBu2-ALAC / tetrahydrofuran / 6 h / 25 °C 2.1: DMAP; pyridine / CH2Cl2 / 2 h / 20 °C 3.1: Dowex50W / methanol / 0.5 h / 50 °C 4.1: Et3N; DMAP / CH2Cl2 / 36 h / 20 °C 5.1: pyridinium p-toluenesulfonate / CH2Cl2 / 12 h / 20 °C 6.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C 7.1: PCC; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C 8.1: NaH / tetrahydrofuran / 0.08 h / 20 °C 8.2: tetrahydrofuran / 1 h 9.1: LiAlH4; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C 10.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C 11.1: 1.0 M aq. NaOH / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme

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

1.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 2.1: Dess-Martin reagent / CH2Cl2 / 2 h / 0 °C 3.1: 54 percent / Ni(cod)2; PPh3; 1,3-cyclohexadiene / iBu2-ALAC / tetrahydrofuran / 6 h / 25 °C 4.1: DMAP; pyridine / CH2Cl2 / 2 h / 20 °C 5.1: Dowex50W / methanol / 0.5 h / 50 °C 6.1: Et3N; DMAP / CH2Cl2 / 36 h / 20 °C 7.1: pyridinium p-toluenesulfonate / CH2Cl2 / 12 h / 20 °C 8.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C 9.1: PCC; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / 0 °C 10.1: NaH / tetrahydrofuran / 0.08 h / 20 °C 10.2: tetrahydrofuran / 1 h 11.1: LiAlH4; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C 12.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C 13.1: 1.0 M aq. NaOH / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme

1: imidazole / dimethylformamide 2: 84 percent / Grubbs' 2nd generation catalyst / CH2Cl2 / 12 h / 40 °C 3: DIBAL-H / CH2Cl2 / -78 °C 4: KOtBu / tetrahydrofuran 5: HCl / tetrahydrofuran / 48 h View Scheme

1: KOtBu / tetrahydrofuran 2: 84 percent / Grubbs' 2nd generation catalyst / CH2Cl2 / 12 h / 40 °C 3: DIBAL-H / CH2Cl2 / -78 °C 4: KOtBu / tetrahydrofuran 5: HCl / tetrahydrofuran / 48 h View Scheme

1: K2CO3 / methanol 2: imidazole / dimethylformamide 3: Et2AlCl / CH2Cl2 / 2 h / -50 °C 4: Dess-Martin periodinane; NaHCO3 / CH2Cl2 5: KOtBu / tetrahydrofuran 6: 84 percent / Grubbs' 2nd generation catalyst / CH2Cl2 / 12 h / 40 °C 7: DIBAL-H / CH2Cl2 / -78 °C 8: KOtBu / tetrahydrofuran 9: HCl / tetrahydrofuran / 48 h View Scheme