argentic oxide; nitric acid in 1,4-dioxane 2.5 h; Ambient temperature;

1: CH2Cl2 / 0.67 h / 20 °C 2: K2CO3; MeOH / 1.5 h / 20 °C 3: 2.9 mg / aq. cerium ammonium nitrate / acetonitrile / 1 h / -10 °C View Scheme

1.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 2.1: CH2Cl2 / 0.17 h / 20 °C 2.2: 97 percent / K2CO3 / methanol / 1.25 h 3.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1.1: 81 percent / diisopropylethylamine; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C 2.1: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 52 h / 20 °C 3.1: CH2Cl2 / 0.17 h / 20 °C 3.2: 97 percent / K2CO3 / methanol / 1.25 h 4.1: 63 percent / aq. ceric ammonium nitrate / acetonitrile / 0.17 h / -10 °C View Scheme

1: 6.60 g / Na2CO3 / dimethylformamide / 25 h / Heating 2: 54 percent / n-BuLi / diethyl ether; hexane / 1.5 h / -78 °C 3: 100 percent / NaH / dimethylformamide / 0 - 20 °C 4: 97 percent / N,N-dimethylbarbituric acid; Pd(PPh3)4 / CH2Cl2 / 2.5 h / Heating 5: 75 percent / Et3N; N,N-dimethylaminopyridine / tetrahydrofuran / 6 h / Heating 6: TBAF / tetrahydrofuran / 24 h / 20 °C 7: 89 percent / diisopropylethylamine / CH2Cl2 / 6 h / -78 °C 8: 72 percent / second generation Grubbs catalyst / toluene / 2 h / Heating 9: DIBAL-H / diethyl ether; hexane / 2 h / -78 °C 10: 52.9 mg / toluene / 3.5 h / Heating 11: TFA / CH2Cl2 / 1.17 h / 0 - 20 °C 12: LiOH; H2O / methanol; tetrahydrofuran / 60 h / 20 °C 13: 6.4 mg / DIPEA; BOPCl / toluene / 37 h / 85 °C 14: CH2Cl2 / 0.67 h / 20 °C 15: K2CO3; MeOH / 1.5 h / 20 °C 16: 2.9 mg / aq. cerium ammonium nitrate / acetonitrile / 1 h / -10 °C View Scheme

1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 4 h 2: 54 percent / n-BuLi / diethyl ether; hexane / 1.5 h / -78 °C 3: 100 percent / NaH / dimethylformamide / 0 - 20 °C 4: 97 percent / N,N-dimethylbarbituric acid; Pd(PPh3)4 / CH2Cl2 / 2.5 h / Heating 5: 75 percent / Et3N; N,N-dimethylaminopyridine / tetrahydrofuran / 6 h / Heating 6: TBAF / tetrahydrofuran / 24 h / 20 °C 7: 89 percent / diisopropylethylamine / CH2Cl2 / 6 h / -78 °C 8: 72 percent / second generation Grubbs catalyst / toluene / 2 h / Heating 9: DIBAL-H / diethyl ether; hexane / 2 h / -78 °C 10: 52.9 mg / toluene / 3.5 h / Heating 11: TFA / CH2Cl2 / 1.17 h / 0 - 20 °C 12: LiOH; H2O / methanol; tetrahydrofuran / 60 h / 20 °C 13: 6.4 mg / DIPEA; BOPCl / toluene / 37 h / 85 °C 14: CH2Cl2 / 0.67 h / 20 °C 15: K2CO3; MeOH / 1.5 h / 20 °C 16: 2.9 mg / aq. cerium ammonium nitrate / acetonitrile / 1 h / -10 °C View Scheme

1: 54 percent / n-BuLi / diethyl ether; hexane / 1.5 h / -78 °C 2: 100 percent / NaH / dimethylformamide / 0 - 20 °C 3: 97 percent / N,N-dimethylbarbituric acid; Pd(PPh3)4 / CH2Cl2 / 2.5 h / Heating 4: 75 percent / Et3N; N,N-dimethylaminopyridine / tetrahydrofuran / 6 h / Heating 5: TBAF / tetrahydrofuran / 24 h / 20 °C 6: 89 percent / diisopropylethylamine / CH2Cl2 / 6 h / -78 °C 7: 72 percent / second generation Grubbs catalyst / toluene / 2 h / Heating 8: DIBAL-H / diethyl ether; hexane / 2 h / -78 °C 9: 52.9 mg / toluene / 3.5 h / Heating 10: TFA / CH2Cl2 / 1.17 h / 0 - 20 °C 11: LiOH; H2O / methanol; tetrahydrofuran / 60 h / 20 °C 12: 6.4 mg / DIPEA; BOPCl / toluene / 37 h / 85 °C 13: CH2Cl2 / 0.67 h / 20 °C 14: K2CO3; MeOH / 1.5 h / 20 °C 15: 2.9 mg / aq. cerium ammonium nitrate / acetonitrile / 1 h / -10 °C View Scheme

1: 54 percent / n-BuLi / diethyl ether; hexane / 1.5 h / -78 °C 2: 100 percent / NaH / dimethylformamide / 0 - 20 °C 3: 97 percent / N,N-dimethylbarbituric acid; Pd(PPh3)4 / CH2Cl2 / 2.5 h / Heating 4: 75 percent / Et3N; N,N-dimethylaminopyridine / tetrahydrofuran / 6 h / Heating 5: TBAF / tetrahydrofuran / 24 h / 20 °C 6: 89 percent / diisopropylethylamine / CH2Cl2 / 6 h / -78 °C 7: 72 percent / second generation Grubbs catalyst / toluene / 2 h / Heating 8: DIBAL-H / diethyl ether; hexane / 2 h / -78 °C 9: 52.9 mg / toluene / 3.5 h / Heating 10: TFA / CH2Cl2 / 1.17 h / 0 - 20 °C 11: LiOH; H2O / methanol; tetrahydrofuran / 60 h / 20 °C 12: 6.4 mg / DIPEA; BOPCl / toluene / 37 h / 85 °C 13: CH2Cl2 / 0.67 h / 20 °C 14: K2CO3; MeOH / 1.5 h / 20 °C 15: 2.9 mg / aq. cerium ammonium nitrate / acetonitrile / 1 h / -10 °C View Scheme

1.1: OsO4; H2O; N-methylmorpholine N-oxide / acetone / 16 h / 20 °C 2.1: aq. NaIO4 / acetone / 2.5 h / 20 °C 3.1: 2.73 g / 4 Angstroem molecular sieves / toluene / 2.5 h / -78 - 0 °C 4.1: 92 percent / KH / tetrahydrofuran / 0 - 20 °C 5.1: OsO4; H2O; N-methylmorpholine N-oxide / acetone / 18 h / 20 °C 6.1: aq. NaIO4 / acetone / 2.5 h / 20 °C 7.1: s-BuLi / tetrahydrofuran; cyclohexane / 4.5 h / -78 - -20 °C 7.2: 1.18 g / citric acid / tetrahydrofuran; cyclohexane; H2O / pH 4 - 5 8.1: BF3*Et2O / tetrahydrofuran; cyclohexane / -78 - -5 °C 8.2: 1.49 g / ethanolamine / pentane / 2.5 h / 0 °C 9.1: 94 percent / 2,6-lutidine / CH2Cl2 / 10 h / -78 °C 10.1: 82 percent / NH4F; MeOH / 9.5 h / Heating 11.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 4 h 12.1: 54 percent / n-BuLi / diethyl ether; hexane / 1.5 h / -78 °C 13.1: 100 percent / NaH / dimethylformamide / 0 - 20 °C 14.1: 97 percent / N,N-dimethylbarbituric acid; Pd(PPh3)4 / CH2Cl2 / 2.5 h / Heating 15.1: 75 percent / Et3N; N,N-dimethylaminopyridine / tetrahydrofuran / 6 h / Heating 16.1: TBAF / tetrahydrofuran / 24 h / 20 °C 17.1: 89 percent / diisopropylethylamine / CH2Cl2 / 6 h / -78 °C 18.1: 72 percent / second generation Grubbs catalyst / toluene / 2 h / Heating 19.1: DIBAL-H / diethyl ether; hexane / 2 h / -78 °C 20.1: 52.9 mg / toluene / 3.5 h / Heating 21.1: TFA / CH2Cl2 / 1.17 h / 0 - 20 °C 22.1: LiOH; H2O / methanol; tetrahydrofuran / 60 h / 20 °C 23.1: 6.4 mg / DIPEA; BOPCl / toluene / 37 h / 85 °C 24.1: CH2Cl2 / 0.67 h / 20 °C 25.1: K2CO3; MeOH / 1.5 h / 20 °C 26.1: 2.9 mg / aq. cerium ammonium nitrate / acetonitrile / 1 h / -10 °C View Scheme

1.1: 2.73 g / 4 Angstroem molecular sieves / toluene / 2.5 h / -78 - 0 °C 2.1: 92 percent / KH / tetrahydrofuran / 0 - 20 °C 3.1: OsO4; H2O; N-methylmorpholine N-oxide / acetone / 18 h / 20 °C 4.1: aq. NaIO4 / acetone / 2.5 h / 20 °C 5.1: s-BuLi / tetrahydrofuran; cyclohexane / 4.5 h / -78 - -20 °C 5.2: 1.18 g / citric acid / tetrahydrofuran; cyclohexane; H2O / pH 4 - 5 6.1: BF3*Et2O / tetrahydrofuran; cyclohexane / -78 - -5 °C 6.2: 1.49 g / ethanolamine / pentane / 2.5 h / 0 °C 7.1: 94 percent / 2,6-lutidine / CH2Cl2 / 10 h / -78 °C 8.1: 82 percent / NH4F; MeOH / 9.5 h / Heating 9.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 4 h 10.1: 54 percent / n-BuLi / diethyl ether; hexane / 1.5 h / -78 °C 11.1: 100 percent / NaH / dimethylformamide / 0 - 20 °C 12.1: 97 percent / N,N-dimethylbarbituric acid; Pd(PPh3)4 / CH2Cl2 / 2.5 h / Heating 13.1: 75 percent / Et3N; N,N-dimethylaminopyridine / tetrahydrofuran / 6 h / Heating 14.1: TBAF / tetrahydrofuran / 24 h / 20 °C 15.1: 89 percent / diisopropylethylamine / CH2Cl2 / 6 h / -78 °C 16.1: 72 percent / second generation Grubbs catalyst / toluene / 2 h / Heating 17.1: DIBAL-H / diethyl ether; hexane / 2 h / -78 °C 18.1: 52.9 mg / toluene / 3.5 h / Heating 19.1: TFA / CH2Cl2 / 1.17 h / 0 - 20 °C 20.1: LiOH; H2O / methanol; tetrahydrofuran / 60 h / 20 °C 21.1: 6.4 mg / DIPEA; BOPCl / toluene / 37 h / 85 °C 22.1: CH2Cl2 / 0.67 h / 20 °C 23.1: K2CO3; MeOH / 1.5 h / 20 °C 24.1: 2.9 mg / aq. cerium ammonium nitrate / acetonitrile / 1 h / -10 °C View Scheme