1: DMAP, pyridine 2: HF, pyridine 3: Jones reagent 5: H2 / Pd/C 6: DBU / 0.33 h / 0 °C View Scheme

1: Jones reagent 3: H2 / Pd/C 4: DBU / 0.33 h / 0 °C View Scheme

1: DMAP, pyridine 2: HF, pyridine 3: Jones reagent 5: H2 / Pd/C 6: DBU / 0.33 h / 0 °C View Scheme

1: H2 / Pd/C 2: DBU / 0.33 h / 0 °C View Scheme

1: HF, pyridine 2: Jones reagent 4: H2 / Pd/C 5: DBU / 0.33 h / 0 °C View Scheme

1: DMAP, pyridine / 48 h 2: DMAP, pyridine 3: HF, pyridine 4: Jones reagent 6: H2 / Pd/C 7: DBU / 0.33 h / 0 °C View Scheme

1,8-diazabicyclo[5.4.0]undec-7-ene T=0°C; 0.333333 h; Yield given;

1: sodium methylate / methanol / 1 h 2: pyridine / 20 °C / |Cooling with ice 3: pyridine / 20 °C / |Cooling with ice 4: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / |Cooling with ice 5: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-piperidine-N-oxyl / acetonitrile; water / 5 h 6: sodium hydrogencarbonate / N,N-dimethyl-formamide 7: palladium dichloride / dichloromethane; methanol / 16 h / 20 °C 8: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 5 h / |Cooling with ice View Scheme

1: pyridine / 20 °C / |Cooling with ice 2: pyridine / 20 °C / |Cooling with ice 3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / |Cooling with ice 4: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-piperidine-N-oxyl / acetonitrile; water / 5 h 5: sodium hydrogencarbonate / N,N-dimethyl-formamide 6: palladium dichloride / dichloromethane; methanol / 16 h / 20 °C 7: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 5 h / |Cooling with ice View Scheme

1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / |Cooling with ice 2: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-piperidine-N-oxyl / acetonitrile; water / 5 h 3: sodium hydrogencarbonate / N,N-dimethyl-formamide 4: palladium dichloride / dichloromethane; methanol / 16 h / 20 °C 5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 5 h / |Cooling with ice View Scheme