1: 47 percent / sodium azide, NH4Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H2O / 6 h / Heating 2: 91 percent / N,N-diisopropylethylamine / CHCl3 / 3 h / Heating 3: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 4: 94 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 5: 92 percent / H2 / 10percent Pd on C / methanol / 2 h / 760 Torr 6: 90 percent / conc. HCl / methanol / 1 h / Heating View Scheme

1: 1.) triethylaluminum / 1.) CH2Cl2, hexane, 30 min, 2.) CH2Cl2, r.t., 14 h 2: 88 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C 3: 85 percent / N,N-diisopropylethylamine / CHCl3 / 1 h / Heating 4: 91 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 5: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -80 deg C, 2 h, 2.) -80 deg C to r.t. 6: 45 percent / TiCl4, molecular sieves 4A / CH2Cl2 / 0.5 h / -80 °C 7: 81 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 8: 83 percent / imidazole / dimethylformamide / 14 h / Ambient temperature 9: 54 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 12 h / Heating 10: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 11: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 12: 80 percent / pyridine / 14 h / Ambient temperature 13: 1.) H2, 2.) Et3N / 1.) Pd(OH)2 / 1.) MeOH, 1 atm, 1 h, 2.) reflux, 1.5 h 14: 71 percent / a) conc. HCl, b) Dowex 1-X8, OH(1-)-form / a) MeOH, reflux, 30 min, b) H2O View Scheme

Multi-step reaction with 4 steps 1: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, from -78 deg to RT2: 1.) NaH / 1.) benzene, RT, 1 h, 2.) benzene, RT, 1 h3: 81 percent / DIBAL / CH2Cl2; toluene / 14 h / Ambient temperature4: 1.) 4A molecular sieves, titanium(IV) isopropoxide, diethyl L-tartrate 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, 2.) CH2Cl2, -20 deg C, 14 h  

Multi-step reaction with 2 steps 1: 81 percent / DIBAL / CH2Cl2; toluene / 14 h / Ambient temperature2: 1.) 4A molecular sieves, titanium(IV) isopropoxide, diethyl L-tartrate 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, 2.) CH2Cl2, -20 deg C, 14 h  

With  titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate  

With  sodium azide; ammonium chloride in  ethylene glycol dimethyl ether; 2-methoxy-ethanol; water 6 h;  Heating;   

Multi-step reaction with 2 steps 1: 47 percent / sodium azide, NH4Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H2O / 6 h / Heating2: 91 percent / N,N-diisopropylethylamine / CHCl3 / 3 h / Heating  

Multi-step reaction with 3 steps 1: 47 percent / sodium azide, NH4Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H2O / 6 h / Heating2: 91 percent / N,N-diisopropylethylamine / CHCl3 / 3 h / Heating3: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature  

Multi-step reaction with 4 steps 1: 47 percent / sodium azide, NH4Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H2O / 6 h / Heating2: 91 percent / N,N-diisopropylethylamine / CHCl3 / 3 h / Heating3: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature4: 94 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C  

Multi-step reaction with 5 steps 1: 47 percent / sodium azide, NH4Cl / 1,2-dimethoxy-ethane; 2-methoxy-ethanol; H2O / 6 h / Heating2: 91 percent / N,N-diisopropylethylamine / CHCl3 / 3 h / Heating3: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature4: 94 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C5: 92 percent / H2 / 10percent Pd on C / methanol / 2 h / 760 Torr