1: Et3N, DMAP / CH2Cl2 2: NaH / tetrahydrofuran / 12 h 3: O3, pyridine / CH2Cl2 5: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 6: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF 7: 75 percent / CBr4, BaCO3, Ph3P / CH2Cl2 / 0.75 h 8: 82 percent / n-Bu3SnH, AIBN / toluene / 1 h / 65 °C 9: 98 percent / PPTs / methanol / 14 h / 22 °C 10: MnO2 / tetrahydrofuran / 5 h 11: NaCN / acetic acid / 16 h View Scheme

Multi-step reaction with 2 steps 1: 85 percent / LiAlH4 / diethyl ether / 1 h / 0 - 22 °C2: 1.) TsCl, DMAP, Et3N, 2.) TsOH, NaOCH3 / 1.) CH2Cl2, 22 deg C, 4 h, 2.) MeOH, 22 deg C, 16 h  

Multi-step reaction with 2 steps 1: Et3N, DMAP / CH2Cl2 2: NaH / tetrahydrofuran / 12 h  

Multi-step reaction with 5 steps 1: Et3N, DMAP / CH2Cl2 2: NaH / tetrahydrofuran / 12 h3: O3, pyridine / CH2Cl2 5: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2  

Multi-step reaction with 6 steps 1: Et3N, DMAP / CH2Cl2 2: NaH / tetrahydrofuran / 12 h3: O3, pyridine / CH2Cl2 5: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 6: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF  

Multi-step reaction with 7 steps 1: Et3N, DMAP / CH2Cl2 2: NaH / tetrahydrofuran / 12 h3: O3, pyridine / CH2Cl2 5: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 6: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF7: 75 percent / CBr4, BaCO3, Ph3P / CH2Cl2 / 0.75 h  

Multi-step reaction with 9 steps 1: Et3N, DMAP / CH2Cl2 2: NaH / tetrahydrofuran / 12 h3: O3, pyridine / CH2Cl2 5: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 6: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF7: 75 percent / CBr4, BaCO3, Ph3P / CH2Cl2 / 0.75 h8: 82 percent / n-Bu3SnH, AIBN / toluene / 1 h / 65 °C9: 98 percent / PPTs / methanol / 14 h / 22 °C  

Multi-step reaction with 10 steps 1: Et3N, DMAP / CH2Cl2 2: NaH / tetrahydrofuran / 12 h3: O3, pyridine / CH2Cl2 5: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 6: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF7: 75 percent / CBr4, BaCO3, Ph3P / CH2Cl2 / 0.75 h8: 82 percent / n-Bu3SnH, AIBN / toluene / 1 h / 65 °C9: 98 percent / PPTs / methanol / 14 h / 22 °C10: MnO2 / tetrahydrofuran / 5 h  

Multi-step reaction with 8 steps 1: Et3N, DMAP / CH2Cl2 2: NaH / tetrahydrofuran / 12 h3: O3, pyridine / CH2Cl2 5: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 6: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF7: 75 percent / CBr4, BaCO3, Ph3P / CH2Cl2 / 0.75 h8: 82 percent / n-Bu3SnH, AIBN / toluene / 1 h / 65 °C  

Multi-step reaction with 11 steps 1: Et3N, DMAP / CH2Cl2 2: NaH / tetrahydrofuran / 12 h3: O3, pyridine / CH2Cl2 5: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 6: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF7: 75 percent / CBr4, BaCO3, Ph3P / CH2Cl2 / 0.75 h8: 82 percent / n-Bu3SnH, AIBN / toluene / 1 h / 65 °C9: 98 percent / PPTs / methanol / 14 h / 22 °C10: MnO2 / tetrahydrofuran / 5 h11: NaCN / acetic acid / 16 h