1: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 2: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min 3: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h 4: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 5: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 6: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C View Scheme

1: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 2: 93 percent / NaClO2, 2-methyl-2-butene, NaH2PO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 4 h / Ambient temperature 3: 1) LDA / 1) THF, -78 deg C, 15 min; -40 deg C, 0.5 h, 2) THF, -78 deg C, 15 min 4: 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 5: 1.1 g / K2CO3 / methanol / 0.25 h / 25 °C 6: 78 percent / TBAF / tetrahydrofuran / 8 h / 25 °C 7: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-DMAP / 1) THF, 0 deg C, 15 min, 2) toluene, 25 deg C, 0.5 h 8: 92 percent / CF3CO2H / CH2Cl2 / 1) -20 deg C -> 0 deg C, 2) 0 deg C, 1 h 9: 65 percent / Na2EDTA, 1,1,1-trifluoroacetone, Oxone, NaHCO3 / acetonitrile; H2O / 0 °C View Scheme

1.1: i-Pr2NH; n-BuLi / tetrahydrofuran; hexane / 0.83 h / -78 °C 1.2: 61 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.1: 89 percent / Et3N / CH2Cl2 / 0.75 h / 0 °C 3.1: OsO4; NaIO4 / tetrahydrofuran; H2O / 18 h 4.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1 h 5.1: 502 mg / methanol; benzene; hexane / 0.75 h 6.1: 92 percent / H2 / Pd/C / ethanol / 0.75 h 7.1: 99 percent / TPAP; NMO / CH2Cl2 / 1 h 8.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / -78 - -30 °C 8.2: 82 percent / tetrahydrofuran; hexane / 70 h / -78 - 20 °C 9.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 10.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 11.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 11.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 12.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 13.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating 14.1: 78 percent / dimethyldioxirane / CH2Cl2 / -50 °C View Scheme

1.1: i-Pr2NH; n-BuLi / tetrahydrofuran; hexane / 0.83 h / -78 °C 1.2: 61 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.1: 89 percent / Et3N / CH2Cl2 / 0.75 h / 0 °C 3.1: OsO4; NaIO4 / tetrahydrofuran; H2O / 18 h 4.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1 h 5.1: 502 mg / methanol; benzene; hexane / 0.75 h 6.1: 92 percent / H2 / Pd/C / ethanol / 0.75 h 7.1: 99 percent / TPAP; NMO / CH2Cl2 / 1 h 8.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / -78 - -30 °C 8.2: 82 percent / tetrahydrofuran; hexane / 70 h / -78 - 20 °C 9.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 10.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 11.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 11.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 12.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 13.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating View Scheme

1: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 2: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min 3: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h 4: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 5: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C View Scheme

1: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 2: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min 3: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h 4: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min 5: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 6: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C 7: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, -78 deg C -> 0 deg C, 30 min 8: 90 percent / NaClO2, isobutylene, NaH2PO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 2: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min 3: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h 4: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min View Scheme

1: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 2: 93 percent / NaClO2, 2-methyl-2-butene, NaH2PO4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 4 h / Ambient temperature 3: 1) LDA / 1) THF, -78 deg C, 15 min; -40 deg C, 0.5 h, 2) THF, -78 deg C, 15 min 4: 2,6-lutidine / CH2Cl2 / 2 h / 0 °C 5: 1.1 g / K2CO3 / methanol / 0.25 h / 25 °C 6: 78 percent / TBAF / tetrahydrofuran / 8 h / 25 °C 7: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-DMAP / 1) THF, 0 deg C, 15 min, 2) toluene, 25 deg C, 0.5 h 8: 92 percent / CF3CO2H / CH2Cl2 / 1) -20 deg C -> 0 deg C, 2) 0 deg C, 1 h View Scheme

1.1: ozone; oxygen / dichloromethane / -78 °C / |Inert atmosphere 2.1: dimethylsulfide / 168 h / 22 °C / |Inert atmosphere 3.1: sodium tetrahydroborate / dichloromethane; ethanol / 2 h / -78 °C / |Inert atmosphere 3.2: 22 °C / |Inert atmosphere 4.1: 1H-imidazole / dichloromethane / 14 h / 22 °C / |Inert atmosphere 5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C / |Inert atmosphere 5.2: 0.25 h / -78 °C / |Inert atmosphere 6.1: 2,6-dimethylpyridine / tetrahydrofuran / 0.5 h / -50 °C / |Inert atmosphere 7.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -78 - -40 °C / |Inert atmosphere 7.2: 0 - 22 °C / |Inert atmosphere 8.1: sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; sodium chlorite / water; tert-butyl alcohol / 3 h / 22 °C / |Inert atmosphere 9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 22 °C / |Inert atmosphere 10.1: C52H67Cl2NOW / benzene; toluene / 2.5 h / 22 °C / 1 Torr / |Inert atmosphere; |Glovebox 11.1: pyridine hydrogenfluoride / tetrahydrofuran / 36 h / 22 °C / |Inert atmosphere View Scheme

1: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h 2: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min 3: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h View Scheme