1: N-chlorosuccinimide, AgNO3, 2,6-lutidine / acetonitrile / 5 min water bath cooling, 45 min stirring 2: LiAlH4 / diethyl ether; tetrahydrofuran / 24 h 3: pyridine / 16 h / 0 °C 4: 60 percent / ethanol; H2O / 1.) add KCN, 0 grad C; 2.) stir overnight, room temp. 5: BH3 / tetrahydrofuran / 1.) add BH3 over 14 min, 0 grad C; 2.) stir 2 h 6: aq. NaOH, 30percent aq. H2O2 / 1 h / 40 °C 7: 1.) 3N aq. NaOH; 2.) 4N aq. H2SO4 / 1.) ca 100 deg C, 20 h; 2.) cool with ice View Scheme

1: AgNO3, N-chlorosuccinimide (NCS), 2,6-lutidine / acetonitrile; H2O / 0.17 h / Ambient temperature 2: NaBH4 / H2O / 2.5 h 3: 83 percent / pyridine / 0 °C 4: KOH / tetrahydrofuran / 1 h / 10 °C 5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, RT,5 h 6: 65 percent / Na2HPO4, 6percent sodium amalgam / methanol / 2.5 h / 25 °C View Scheme

1: N-chlorosuccinimide, AgNO3, 2,6-lutidine / acetonitrile / 5 min water bath cooling, 45 min stirring 2: LiAlH4 / diethyl ether; tetrahydrofuran / 24 h 3: pyridine / 16 h / 0 °C 4: 60 percent / ethanol; H2O / 1.) add KCN, 0 grad C; 2.) stir overnight, room temp. View Scheme

1: N-chlorosuccinimide, AgNO3, 2,6-lutidine / acetonitrile / 5 min water bath cooling, 45 min stirring 2: LiAlH4 / diethyl ether; tetrahydrofuran / 24 h 3: pyridine / 16 h / 0 °C 4: 60 percent / ethanol; H2O / 1.) add KCN, 0 grad C; 2.) stir overnight, room temp. 5: BH3 / tetrahydrofuran / 1.) add BH3 over 14 min, 0 grad C; 2.) stir 2 h View Scheme

Multi-step reaction with 4 steps 1: AgNO3, N-chlorosuccinimide (NCS), 2,6-lutidine / acetonitrile; H2O / 0.17 h / Ambient temperature2: NaBH4 / H2O / 2.5 h3: 83 percent / pyridine / 0 °C4: KOH / tetrahydrofuran / 1 h / 10 °C  

Multi-step reaction with 6 steps 1: AgNO3, N-chlorosuccinimide (NCS), 2,6-lutidine / acetonitrile; H2O / 0.17 h / Ambient temperature2: NaBH4 / H2O / 2.5 h3: 83 percent / pyridine / 0 °C4: KOH / tetrahydrofuran / 1 h / 10 °C5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, RT,5 h6: Na2HPO4, 6percent sodium amalgam / methanol / 2.5 h / 25 °C