1: 73.2 percent / H2 / 5percent Pd-BaSO4 / pyridine / 8 h / Ambient temperature 2: 91 percent / tetrabutylammonium fluoride, 48percent aq. HF / pyridine / 4 h / Ambient temperature 3: 84 percent / Et3N / CH2Cl2 / 1 h / 0 °C 4: 80 percent / LiBr / tetrahydrofuran / 14 h / Ambient temperature 5: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 6: 72 percent / TsOH, MeOH / 4 h / Ambient temperature 7: Et3N / CH2Cl2 / 1 h / 0 °C 8: LiBr / tetrahydrofuran / Ambient temperature 9: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h 10: H2 / Lindlar catalyst, quinoline / toluene / 2 h / Ambient temperature 11: H2O, Rhisopus arrhizus lipase / 2 h / 25 °C / pH 7.02 View Scheme

Multi-step reaction with 2 steps 1: 76 percent / NaI / acetone / 2 h / Heating2: n-BuLi / hexane  

Multi-step reaction with 2 steps 1: 73.2 percent / H2 / 5percent Pd-BaSO4 / pyridine / 8 h / Ambient temperature2: 91 percent / tetrabutylammonium fluoride, 48percent aq. HF / pyridine / 4 h / Ambient temperature  

Multi-step reaction with 4 steps 1: 73.2 percent / H2 / 5percent Pd-BaSO4 / pyridine / 8 h / Ambient temperature2: 91 percent / tetrabutylammonium fluoride, 48percent aq. HF / pyridine / 4 h / Ambient temperature3: 84 percent / Et3N / CH2Cl2 / 1 h / 0 °C4: 80 percent / LiBr / tetrahydrofuran / 14 h / Ambient temperature  

Multi-step reaction with 5 steps 1: 73.2 percent / H2 / 5percent Pd-BaSO4 / pyridine / 8 h / Ambient temperature2: 91 percent / tetrabutylammonium fluoride, 48percent aq. HF / pyridine / 4 h / Ambient temperature3: 84 percent / Et3N / CH2Cl2 / 1 h / 0 °C4: 80 percent / LiBr / tetrahydrofuran / 14 h / Ambient temperature5: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h  

Multi-step reaction with 6 steps 1: 73.2 percent / H2 / 5percent Pd-BaSO4 / pyridine / 8 h / Ambient temperature2: 91 percent / tetrabutylammonium fluoride, 48percent aq. HF / pyridine / 4 h / Ambient temperature3: 84 percent / Et3N / CH2Cl2 / 1 h / 0 °C4: 80 percent / LiBr / tetrahydrofuran / 14 h / Ambient temperature5: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h6: 72 percent / TsOH, MeOH / 4 h / Ambient temperature  

Multi-step reaction with 7 steps 1: 73.2 percent / H2 / 5percent Pd-BaSO4 / pyridine / 8 h / Ambient temperature2: 91 percent / tetrabutylammonium fluoride, 48percent aq. HF / pyridine / 4 h / Ambient temperature3: 84 percent / Et3N / CH2Cl2 / 1 h / 0 °C4: 80 percent / LiBr / tetrahydrofuran / 14 h / Ambient temperature5: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h6: 72 percent / TsOH, MeOH / 4 h / Ambient temperature7: Et3N / CH2Cl2 / 1 h / 0 °C  

Multi-step reaction with 8 steps 1: 73.2 percent / H2 / 5percent Pd-BaSO4 / pyridine / 8 h / Ambient temperature2: 91 percent / tetrabutylammonium fluoride, 48percent aq. HF / pyridine / 4 h / Ambient temperature3: 84 percent / Et3N / CH2Cl2 / 1 h / 0 °C4: 80 percent / LiBr / tetrahydrofuran / 14 h / Ambient temperature5: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h6: 72 percent / TsOH, MeOH / 4 h / Ambient temperature7: Et3N / CH2Cl2 / 1 h / 0 °C8: LiBr / tetrahydrofuran / Ambient temperature  

Multi-step reaction with 9 steps 1: 73.2 percent / H2 / 5percent Pd-BaSO4 / pyridine / 8 h / Ambient temperature2: 91 percent / tetrabutylammonium fluoride, 48percent aq. HF / pyridine / 4 h / Ambient temperature3: 84 percent / Et3N / CH2Cl2 / 1 h / 0 °C4: 80 percent / LiBr / tetrahydrofuran / 14 h / Ambient temperature5: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h6: 72 percent / TsOH, MeOH / 4 h / Ambient temperature7: Et3N / CH2Cl2 / 1 h / 0 °C8: LiBr / tetrahydrofuran / Ambient temperature9: 1.) copper(II) sulfate heptahydrate, hydroxylamine hydrochloride, ammonium hydroxyde, 2.) NaCN / 1.) water-ethanol, 5 min, 2.) DMF, r.t., 5 h