tetrabutyl ammonium fluoride in tetrahydrofuran T=0°C; 2 h;

1.1: NaH / dimethylformamide / -20 - 20 °C 2.1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 4.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 6.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 7.1: 73 percent / benzene / 48 h / 80 °C 8.1: 84 percent / benzene / 39 h / 70 °C 9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 10.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 13.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: DMAP / pentane / 168 h / 20 °C 14.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 15.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 17.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 18.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 19.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 22.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 23.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 24.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 25.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 26.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: 98 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C 2.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 3.1: imidazole / dimethylformamide / 0 - 20 °C 4.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 5.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 6.2: tetrahydrofuran; hexane / 1 h / -30 °C 6.3: tetrahydrofuran; hexane / -20 °C 7.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 8.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 9.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 10.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 11.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 12.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 13.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 14.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 15.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 17.1: Et3N / benzene / 1 h / 20 °C 18.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 19.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 20.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 21.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 21.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: DMAP / pentane / 168 h / 20 °C 22.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 23.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 24.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 25.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 26.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 27.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 28.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 29.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 30.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 31.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 32.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 33.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 34.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: imidazole / dimethylformamide / 0 - 20 °C 2.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 3.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 4.2: tetrahydrofuran; hexane / 1 h / -30 °C 4.3: tetrahydrofuran; hexane / -20 °C 5.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 6.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 7.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 8.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 9.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 10.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 11.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 13.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 14.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 15.1: Et3N / benzene / 1 h / 20 °C 16.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 17.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 18.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 19.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 19.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: DMAP / pentane / 168 h / 20 °C 20.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 21.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 22.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 23.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 24.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 25.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 26.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 27.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 28.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 29.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 30.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 31.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 32.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 2.2: tetrahydrofuran; hexane / 1 h / -30 °C 2.3: tetrahydrofuran; hexane / -20 °C 3.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 4.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 5.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 6.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 7.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 8.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 9.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 10.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 11.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 13.1: Et3N / benzene / 1 h / 20 °C 14.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 15.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 16.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 17.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 17.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18.1: DMAP / pentane / 168 h / 20 °C 18.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 19.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 20.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 21.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 22.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 23.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 24.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 25.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 26.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 27.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 28.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 29.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 30.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 1.2: tetrahydrofuran; hexane / 1 h / -30 °C 1.3: tetrahydrofuran; hexane / -20 °C 2.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 3.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 4.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 5.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 6.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 7.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 8.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 9.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 10.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 11.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 12.1: Et3N / benzene / 1 h / 20 °C 13.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 14.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 15.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 16.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 16.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: DMAP / pentane / 168 h / 20 °C 17.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 18.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 19.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 20.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 21.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 22.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 25.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 26.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 27.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 28.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 29.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 2.1: imidazole / dimethylformamide / 0 - 20 °C 3.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 4.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 5.2: tetrahydrofuran; hexane / 1 h / -30 °C 5.3: tetrahydrofuran; hexane / -20 °C 6.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 7.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 8.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 9.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 10.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 11.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 12.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 13.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 14.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 16.1: Et3N / benzene / 1 h / 20 °C 17.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 18.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 19.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 20.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 20.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: DMAP / pentane / 168 h / 20 °C 21.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 22.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 23.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 24.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 25.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 26.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 27.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 28.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 29.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 30.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 31.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 32.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 33.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 2.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 3.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 4.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 5.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 6.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 7.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 8.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 9.1: Et3N / benzene / 1 h / 20 °C 10.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 13.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: DMAP / pentane / 168 h / 20 °C 14.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 15.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 17.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 18.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 19.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 22.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 23.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 24.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 25.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 26.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 2.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 3.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 4.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 5.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 6.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 7.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 8.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 9.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 10.1: Et3N / benzene / 1 h / 20 °C 11.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 12.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 13.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 14.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 14.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 15.1: DMAP / pentane / 168 h / 20 °C 15.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 16.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 17.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 18.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 19.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 20.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 21.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 23.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 24.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 25.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 26.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 27.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme

1.1: 92 percent / LiAlH4 / diethyl ether / 12 h / 25 °C 2.1: 84 percent / imidazole; DMAP / CH2Cl2 / 8 h / 25 °C 3.1: 89 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 25 °C 4.1: toluene / 1 h / -78 °C 4.2: NaH / tetrahydrofuran / 1 h / 0 °C 4.3: TBAI / tetrahydrofuran / 12 h / 25 °C 5.1: 93 percent / TBAF / tetrahydrofuran / 12 h / 25 °C 6.1: 93 percent / iPr2NEt / CH2Cl2 / 8 h / 0 - 25 °C 7.1: OsO4; NMO; pyridine / acetone; H2O / 12 h / 25 °C 7.2: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / 25 °C 8.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 8.2: 77 percent / tetrahydrofuran / 2 h / -78 °C 9.1: 98 percent / TBAF / tetrahydrofuran / 0.5 h / 25 °C 10.1: 91 percent / DDQ / CH2Cl2 / 1 h / 25 °C / pH 7.0 11.1: 93 percent / imidazole; DMAP / CH2Cl2 / 8 h / 40 °C 12.1: n-BuLi / hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 0.5 h / -78 °C 12.2: hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 1 h / -78 °C 13.1: Ph2S / sunlight 14.1: 98 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 25 °C 15.1: 89 percent / DDQ / H2O; CH2Cl2 / 0.5 h / 25 °C / pH 7.0 16.1: 94 percent / TEMPO; bis(acetoxy)iodobenzene / CH2Cl2 / 2 h / 25 °C 17.1: BF3*OEt2 / tetrahydrofuran / 1 h / -78 °C 18.1: 86 percent / iPr2NEt / CH2Cl2 / 12 h / 25 °C 19.1: 88 percent / HF*pyridine / tetrahydrofuran / 12 h / 25 °C 20.1: 83 percent / CF3COOH / CH2Cl2 / 3 h / 0 °C 21.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 25 °C 21.2: 59 percent / DMAP / tetrahydrofuran; toluene / 12 h / 25 °C 22.1: hydroquinone; nBu3SnH / Mo(CO)3(tBuNC)3 / tetrahydrofuran / 12 h / 55 °C 22.2: 54 percent / I2 / CH2Cl2 / 25 °C 23.1: 90 percent / CuI / Pd(PPh3)4 / toluene / 8 h / 80 °C 24.1: 69 percent / Me2BBr / CH2Cl2 / 2 h / -78 °C 25.1: 85 percent / TEMPO; TCCA / CH2Cl2 / 1 h / 25 °C 26.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 0.5 h / 25 °C 27.1: NaBH4; CeCl3*7H2O / methanol / 1 h / 0 °C View Scheme