1.1: 25 percent / LiAlH4 / -78 °C 2.1: 86 percent / DCC; DMAP / CH2Cl2 / 1 h / 0 °C 3.1: disiamylborane / tetrahydrofuran / 0 - 20 °C 3.2: 74 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0.33 h / 10 - 20 °C 4.1: 89 percent / pyridine / 12 h / 0 - 20 °C 5.1: 88 percent / MsN3; Et3N / acetonitrile / 10 h / 20 °C 6.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating 7.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C 8.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C 9.1: 98 percent / Jones reagent / acetone / 0 °C 10.1: DCC / CH2Cl2 / 1 h / 0 °C 10.2: 67 percent / CH2Cl2 / 15 h / 20 °C 11.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C 12.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C 13.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C 13.2: 18.7 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C 14.1: 96 percent / Me3SiCl / methanol / 3 h / 0 - 20 °C 15.1: 30 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 16.1: Py*SO3; Et3N / dimethylsulfoxide / 20 h / 20 °C 17.1: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C View Scheme

Multi-step reaction with 14 steps 1.1: 25 percent / LiAlH4 / -78 °C2.1: 86 percent / DCC; DMAP / CH2Cl2 / 1 h / 0 °C3.1: disiamylborane / tetrahydrofuran / 0 - 20 °C3.2: 74 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0.33 h / 10 - 20 °C4.1: 89 percent / pyridine / 12 h / 0 - 20 °C5.1: 88 percent / MsN3; Et3N / acetonitrile / 10 h / 20 °C6.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating7.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C8.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C9.1: 98 percent / Jones reagent / acetone / 0 °C10.1: DCC / CH2Cl2 / 1 h / 0 °C10.2: 67 percent / CH2Cl2 / 15 h / 20 °C11.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C12.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C13.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C13.2: 18.7 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C14.1: 96 percent / Me3SiCl / methanol / 3 h / 0 - 20 °C  

Multi-step reaction with 14 steps 1.1: 50 percent / LiAlH4 / -5 °C2.1: 86 percent / DCC; DMAP / CH2Cl2 / 1 h / 0 °C3.1: disiamylborane / tetrahydrofuran / 0 - 20 °C3.2: 74 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0.33 h / 10 - 20 °C4.1: 89 percent / pyridine / 12 h / 0 - 20 °C5.1: 88 percent / MsN3; Et3N / acetonitrile / 10 h / 20 °C6.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating7.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C8.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C9.1: 98 percent / Jones reagent / acetone / 0 °C10.1: DCC / CH2Cl2 / 1 h / 0 °C10.2: 67 percent / CH2Cl2 / 15 h / 20 °C11.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C12.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C13.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C13.2: 49.4 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C14.1: 21 mg / BF3*OEt2 / 10 h / 40 °C  

With  lithium aluminium tetrahydride in  tetrahydrofuran T=0°C; 6 h;