1.1: 86 percent / DCC; DMAP / CH2Cl2 / 1 h / 0 °C 2.1: disiamylborane / tetrahydrofuran / 0 - 20 °C 2.2: 74 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0.33 h / 10 - 20 °C 3.1: 89 percent / pyridine / 12 h / 0 - 20 °C 4.1: 88 percent / MsN3; Et3N / acetonitrile / 10 h / 20 °C 5.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating 6.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C 7.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C 8.1: 98 percent / Jones reagent / acetone / 0 °C 9.1: DCC / CH2Cl2 / 1 h / 0 °C 9.2: 67 percent / CH2Cl2 / 15 h / 20 °C 10.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C 11.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C 12.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C 12.2: 18.7 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C 13.1: 96 percent / Me3SiCl / methanol / 3 h / 0 - 20 °C 14.1: 30 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 15.1: Py*SO3; Et3N / dimethylsulfoxide / 20 h / 20 °C 16.1: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C View Scheme

1.1: disiamylborane / tetrahydrofuran / 0 - 20 °C 1.2: 74 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0.33 h / 10 - 20 °C 2.1: 89 percent / pyridine / 12 h / 0 - 20 °C 3.1: 88 percent / MsN3; Et3N / acetonitrile / 10 h / 20 °C 4.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating 5.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C 6.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C 7.1: 98 percent / Jones reagent / acetone / 0 °C 8.1: DCC / CH2Cl2 / 1 h / 0 °C 8.2: 67 percent / CH2Cl2 / 15 h / 20 °C 9.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C 10.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C 11.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C 11.2: 18.7 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C 12.1: 96 percent / Me3SiCl / methanol / 3 h / 0 - 20 °C 13.1: 30 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 14.1: Py*SO3; Et3N / dimethylsulfoxide / 20 h / 20 °C 15.1: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C View Scheme

1.1: 89 percent / pyridine / 12 h / 0 - 20 °C 2.1: 88 percent / MsN3; Et3N / acetonitrile / 10 h / 20 °C 3.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating 4.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C 5.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C 6.1: 98 percent / Jones reagent / acetone / 0 °C 7.1: DCC / CH2Cl2 / 1 h / 0 °C 7.2: 67 percent / CH2Cl2 / 15 h / 20 °C 8.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C 9.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C 10.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C 10.2: 18.7 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C 11.1: 96 percent / Me3SiCl / methanol / 3 h / 0 - 20 °C 12.1: 30 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 13.1: Py*SO3; Et3N / dimethylsulfoxide / 20 h / 20 °C 14.1: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C View Scheme

1.1: 88 percent / MsN3; Et3N / acetonitrile / 10 h / 20 °C 2.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating 3.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C 4.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C 5.1: 98 percent / Jones reagent / acetone / 0 °C 6.1: DCC / CH2Cl2 / 1 h / 0 °C 6.2: 67 percent / CH2Cl2 / 15 h / 20 °C 7.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C 8.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C 9.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C 9.2: 18.7 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C 10.1: 96 percent / Me3SiCl / methanol / 3 h / 0 - 20 °C 11.1: 30 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 12.1: Py*SO3; Et3N / dimethylsulfoxide / 20 h / 20 °C 13.1: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C View Scheme

pyridine; chromium(VI) oxide; lithium aluminium tetrahydride 1) ether, reflux, 2 h 2) r.t., 30 min; Yield given. Multistep reaction;

in hydrogenchloride; water T=80°C; 0.5 h; Heating;

1: TiCl3 / 1,2-dimethoxy-ethane 2: 1.) NaBH4; 2.) 9percent HCl / 2.) reflux 3: CrO3/H2SO4 / acetone 4: diisobutylaluminum hydride (DIBAH) / diethyl ether 5: p-TsOH / Heating 6: 1.) AcOH; 2.) NaOH / 1.) reflux; 2.) MeOH 7: 53 percent / CrO3/pyridine 8: LiAlH4 / diethyl ether 9: CrO3/pyridine View Scheme

1: 1.) AcOH; 2.) NaOH / 1.) reflux; 2.) MeOH 2: 53 percent / CrO3/pyridine 3: LiAlH4 / diethyl ether 4: CrO3/pyridine View Scheme

1: 1.) NaBH4; 2.) 9percent HCl / 2.) reflux 2: CrO3/H2SO4 / acetone 3: diisobutylaluminum hydride (DIBAH) / diethyl ether 4: p-TsOH / Heating 5: 1.) AcOH; 2.) NaOH / 1.) reflux; 2.) MeOH 6: 53 percent / CrO3/pyridine 7: LiAlH4 / diethyl ether 8: CrO3/pyridine View Scheme

1: diisobutylaluminum hydride (DIBAH) / diethyl ether 2: p-TsOH / Heating 3: 1.) AcOH; 2.) NaOH / 1.) reflux; 2.) MeOH 4: 53 percent / CrO3/pyridine 5: LiAlH4 / diethyl ether 6: CrO3/pyridine View Scheme