1: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 2: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C 3: K2CO3; MeOH / 15 h / 20 °C 4: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 5: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 6: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 7: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1: K2CO3; MeOH / 15 h / 20 °C 2: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 3: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 4: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 5: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 2: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 3: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1.1: tetrahydrofuran / 48 h / 20 °C 2.1: tetrahydrofuran / 11.5 h / -78 - 20 °C 2.2: 80.4 percent / ethanolamine / tetrahydrofuran / 8 h / 20 °C 3.1: aq. HCl / tetrahydrofuran / 10 h / 60 °C 4.1: NaBH4 / tetrahydrofuran; H2O / 0.5 h / 20 °C 5.1: 136 mg / triethylamine / CH2Cl2 / 10 h / 20 °C 6.1: 94 percent / 1,3-propanedithiol; aq. HCl / 2,2,2-trifluoro-ethanol / 4 h / 60 °C 7.1: 53 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 8.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 9.1: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C 10.1: K2CO3; MeOH / 15 h / 20 °C 11.1: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 12.1: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 13.1: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 14.1: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1.1: tetrahydrofuran / 11.5 h / -78 - 20 °C 1.2: 80.4 percent / ethanolamine / tetrahydrofuran / 8 h / 20 °C 2.1: aq. HCl / tetrahydrofuran / 10 h / 60 °C 3.1: NaBH4 / tetrahydrofuran; H2O / 0.5 h / 20 °C 4.1: 136 mg / triethylamine / CH2Cl2 / 10 h / 20 °C 5.1: 94 percent / 1,3-propanedithiol; aq. HCl / 2,2,2-trifluoro-ethanol / 4 h / 60 °C 6.1: 53 percent / triethylamine / CH2Cl2 / 12 h / 20 °C 7.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 8.1: 66 mg / NaH2PO4; NaClO2; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1.5 h / 0 °C 9.1: K2CO3; MeOH / 15 h / 20 °C 10.1: 42.5 mg / pyridine; BOPCl / acetonitrile / 2 h / 20 °C 11.1: 57 percent / pyridine; Ph3PCl2 / acetonitrile / 18 h / 20 °C 12.1: 60 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 13.1: 56 percent / EXP-B1Y ketoreductase; NAD(1+); glucose dehydrogenase / glucose / dimethylsulfoxide; aq. phosphate buffer / 0.67 h / 37 - 39 °C / pH 6.9 View Scheme

1: With Fe2(S04)3; oxygen; calcium carbonate; potassium bromide; yeast extract; strain CNB476 in water T=28°C; 24 h; Microbiological reaction; 2: in water T=28°C; 120 h; Microbiological reaction; Product distribution / selectivity;

1: 70.0 mg / NaBH4 / tetrahydrofuran; H2O / 0.5 h 2: BCl3 / CH2Cl2 / 0.5 h / 0 °C 3: BOPCl; TEA / CH2Cl2 / 16 h / 20 °C 4: 6.8 mg / PH3PCl2 / pyridine; acetonitrile / 4 h / 20 °C View Scheme

1: BCl3 / CH2Cl2 / 0.5 h / 0 °C 2: BOPCl; TEA / CH2Cl2 / 16 h / 20 °C 3: 6.8 mg / PH3PCl2 / pyridine; acetonitrile / 4 h / 20 °C View Scheme

1: 88 percent / tetrahydrofuran; hexane / 3 h / -78 °C 2: 90 percent / CAN / H2O; acetonitrile / 6 h / 0 °C 3: liq. NH3; Na / tetrahydrofuran / 2 h / -78 °C 4: 70.0 mg / NaBH4 / tetrahydrofuran; H2O / 0.5 h 5: BCl3 / CH2Cl2 / 0.5 h / 0 °C 6: BOPCl; TEA / CH2Cl2 / 16 h / 20 °C 7: 6.8 mg / PH3PCl2 / pyridine; acetonitrile / 4 h / 20 °C View Scheme

1: liq. NH3; Na / tetrahydrofuran / 2 h / -78 °C 2: 70.0 mg / NaBH4 / tetrahydrofuran; H2O / 0.5 h 3: BCl3 / CH2Cl2 / 0.5 h / 0 °C 4: BOPCl; TEA / CH2Cl2 / 16 h / 20 °C 5: 6.8 mg / PH3PCl2 / pyridine; acetonitrile / 4 h / 20 °C View Scheme