1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 2.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 2.2: 20 °C / |Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / |Inert atmosphere View Scheme

1.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 0.17 h / 20 °C / |Inert atmosphere 1.2: |Inert atmosphere 2.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C / |Inert atmosphere 2.2: 0.33 h / -78 °C 3.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.08 h / 0 °C / |Inert atmosphere 3.2: 0.17 h / |Inert atmosphere 4.1: ozone; triethylamine / dichloromethane / 3 h / -78 - 20 °C / |Inert atmosphere 5.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / |Inert atmosphere 5.2: 1 h / -78 °C / |Inert atmosphere 5.3: 3 h / -78 - 20 °C / |Inert atmosphere 6.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / |Inert atmosphere 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 8.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 8.2: 20 °C / |Inert atmosphere 9.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / |Inert atmosphere View Scheme

1.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C / |Inert atmosphere 1.2: 0.33 h / -78 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.08 h / 0 °C / |Inert atmosphere 2.2: 0.17 h / |Inert atmosphere 3.1: ozone; triethylamine / dichloromethane / 3 h / -78 - 20 °C / |Inert atmosphere 4.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / |Inert atmosphere 4.2: 1 h / -78 °C / |Inert atmosphere 4.3: 3 h / -78 - 20 °C / |Inert atmosphere 5.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / |Inert atmosphere 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 7.2: 20 °C / |Inert atmosphere 8.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / |Inert atmosphere View Scheme

1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.08 h / 0 °C / |Inert atmosphere 1.2: 0.17 h / |Inert atmosphere 2.1: ozone; triethylamine / dichloromethane / 3 h / -78 - 20 °C / |Inert atmosphere 3.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / |Inert atmosphere 3.2: 1 h / -78 °C / |Inert atmosphere 3.3: 3 h / -78 - 20 °C / |Inert atmosphere 4.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / |Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 6.2: 20 °C / |Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / |Inert atmosphere View Scheme

1.1: ozone; triethylamine / dichloromethane / 3 h / -78 - 20 °C / |Inert atmosphere 2.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / |Inert atmosphere 2.2: 1 h / -78 °C / |Inert atmosphere 2.3: 3 h / -78 - 20 °C / |Inert atmosphere 3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / |Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 5.2: 20 °C / |Inert atmosphere 6.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / |Inert atmosphere View Scheme

1.1: C21H27NO; N,N-diethylaniline; benzo[1,3,2]dioxaborole / toluene / 4 h / -60 °C / |Inert atmosphere 2.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 0.17 h / 20 °C / |Inert atmosphere 2.2: |Inert atmosphere 3.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C / |Inert atmosphere 3.2: 0.33 h / -78 °C 4.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.08 h / 0 °C / |Inert atmosphere 4.2: 0.17 h / |Inert atmosphere 5.1: ozone; triethylamine / dichloromethane / 3 h / -78 - 20 °C / |Inert atmosphere 6.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / |Inert atmosphere 6.2: 1 h / -78 °C / |Inert atmosphere 6.3: 3 h / -78 - 20 °C / |Inert atmosphere 7.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / |Inert atmosphere 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / |Inert atmosphere 9.2: 20 °C / |Inert atmosphere 10.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / |Inert atmosphere View Scheme

1.1: imid. 2.1: 78 percent / i-Pr2EtN 3.1: Bu3SnH; AIBN 3.2: SnBr4 / -78 °C 4.1: 80 percent / pyridine 5.1: 59 percent / Bu3SnH; AIBN 6.1: 91 percent / DDQ 7.1: 97 percent / Bu4NF 8.1: Dess-Martin periodinane 9.1: 99 percent / Dess-Martin periodinane 10.1: 74 percent / n-BuLi 11.1: DIBAL-H 12.1: Dess-Martin periodinane 13.1: 67 percent / Li(i-Pr)2N / -78 °C 14.1: 79 percent / Cl2CHCO2H 15.1: Dess-Martin periodinane 16.1: NaClO2 17.1: MgBr2; n-BuSH; K2CO3 18.1: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 19.1: 91 percent / CF3CO2H / CH2Cl2 View Scheme

1: i-Pr2EtN; DMAP 2: 89 percent / Dess-Martin periodinane 3: 67 percent / Li(i-Pr)2N / -78 °C 4: 79 percent / Cl2CHCO2H 5: Dess-Martin periodinane 6: NaClO2 7: MgBr2; n-BuSH; K2CO3 8: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 9: 91 percent / CF3CO2H / CH2Cl2 View Scheme

1.1: 78 percent / i-Pr2EtN 2.1: Bu3SnH; AIBN 2.2: SnBr4 / -78 °C 3.1: 80 percent / pyridine 4.1: 59 percent / Bu3SnH; AIBN 5.1: 91 percent / DDQ 6.1: 97 percent / Bu4NF 7.1: Dess-Martin periodinane 8.1: 99 percent / Dess-Martin periodinane 9.1: 74 percent / n-BuLi 10.1: DIBAL-H 11.1: Dess-Martin periodinane 12.1: 67 percent / Li(i-Pr)2N / -78 °C 13.1: 79 percent / Cl2CHCO2H 14.1: Dess-Martin periodinane 15.1: NaClO2 16.1: MgBr2; n-BuSH; K2CO3 17.1: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 18.1: 91 percent / CF3CO2H / CH2Cl2 View Scheme

1: 99 percent / Dess-Martin periodinane 2: 74 percent / n-BuLi 3: DIBAL-H 4: Dess-Martin periodinane 5: 67 percent / Li(i-Pr)2N / -78 °C 6: 79 percent / Cl2CHCO2H 7: Dess-Martin periodinane 8: NaClO2 9: MgBr2; n-BuSH; K2CO3 10: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 11: 91 percent / CF3CO2H / CH2Cl2 View Scheme