1.1: K2CO3 / acetonitrile; toluene / 18 h / 20 °C 2.1: 1.34 g / pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 3.1: CH2Cl2 / 1 h / 20 °C 3.2: 4-methylmorpholine N-oxide monohydrate / acetonitrile / 4 h / 20 °C 4.1: 542 mg / H2 / Pd/C / methanol / 1 h / 760 Torr 5.1: HMDS / CH2Cl2 / 1.25 h / -20 - 20 °C 6.1: 779 mg / tetrahydrofuran / 4 h / -78 - 20 °C 7.1: 60 percent / mCPBA / tetrahydrofuran / 1.5 h / -40 - 20 °C 8.1: 77 percent / toluene / 1 h / 70 °C 9.1: NaBH4 / ethanol / 5 h / 20 °C 10.1: 77 percent / DMAP / CH2Cl2 / 2 h / 20 °C 11.1: 83 percent / Bu3SnH; 1,1'-azobis(cyclohexanecarbonitrile) / toluene / 2 h / Heating 12.1: NaOMe / methanol / 24 h / 100 °C 13.1: 8 mg / PTSA / dioxane; H2O / 24 h / 120 °C View Scheme

1.1: 570 mg / KOH; H2O / ethanol / 2 h / Heating 2.1: K2CO3 / acetonitrile; toluene / 18 h / 20 °C 3.1: 1.34 g / pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 4.1: CH2Cl2 / 1 h / 20 °C 4.2: 4-methylmorpholine N-oxide monohydrate / acetonitrile / 4 h / 20 °C 5.1: 542 mg / H2 / Pd/C / methanol / 1 h / 760 Torr 6.1: HMDS / CH2Cl2 / 1.25 h / -20 - 20 °C 7.1: 779 mg / tetrahydrofuran / 4 h / -78 - 20 °C 8.1: 60 percent / mCPBA / tetrahydrofuran / 1.5 h / -40 - 20 °C 9.1: 77 percent / toluene / 1 h / 70 °C 10.1: NaBH4 / ethanol / 5 h / 20 °C 11.1: 77 percent / DMAP / CH2Cl2 / 2 h / 20 °C 12.1: 83 percent / Bu3SnH; 1,1'-azobis(cyclohexanecarbonitrile) / toluene / 2 h / Heating 13.1: NaOMe / methanol / 24 h / 100 °C 14.1: 8 mg / PTSA / dioxane; H2O / 24 h / 120 °C View Scheme

1.1: CH2Cl2 / 1 h / 20 °C 1.2: 4-methylmorpholine N-oxide monohydrate / acetonitrile / 4 h / 20 °C 2.1: 542 mg / H2 / Pd/C / methanol / 1 h / 760 Torr 3.1: HMDS / CH2Cl2 / 1.25 h / -20 - 20 °C 4.1: 779 mg / tetrahydrofuran / 4 h / -78 - 20 °C 5.1: 60 percent / mCPBA / tetrahydrofuran / 1.5 h / -40 - 20 °C 6.1: 77 percent / toluene / 1 h / 70 °C 7.1: NaBH4 / ethanol / 5 h / 20 °C 8.1: 77 percent / DMAP / CH2Cl2 / 2 h / 20 °C 9.1: 83 percent / Bu3SnH; 1,1'-azobis(cyclohexanecarbonitrile) / toluene / 2 h / Heating 10.1: NaOMe / methanol / 24 h / 100 °C 11.1: 8 mg / PTSA / dioxane; H2O / 24 h / 120 °C View Scheme

1.1: 71 percent / Bu3SnH; 1,1'-azobis(cyclohexanecarbonitrile) / toluene / 3 h / Heating 2.1: 570 mg / KOH; H2O / ethanol / 2 h / Heating 3.1: K2CO3 / acetonitrile; toluene / 18 h / 20 °C 4.1: 1.34 g / pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 5.1: CH2Cl2 / 1 h / 20 °C 5.2: 4-methylmorpholine N-oxide monohydrate / acetonitrile / 4 h / 20 °C 6.1: 542 mg / H2 / Pd/C / methanol / 1 h / 760 Torr 7.1: HMDS / CH2Cl2 / 1.25 h / -20 - 20 °C 8.1: 779 mg / tetrahydrofuran / 4 h / -78 - 20 °C 9.1: 60 percent / mCPBA / tetrahydrofuran / 1.5 h / -40 - 20 °C 10.1: 77 percent / toluene / 1 h / 70 °C 11.1: NaBH4 / ethanol / 5 h / 20 °C 12.1: 77 percent / DMAP / CH2Cl2 / 2 h / 20 °C 13.1: 83 percent / Bu3SnH; 1,1'-azobis(cyclohexanecarbonitrile) / toluene / 2 h / Heating 14.1: NaOMe / methanol / 24 h / 100 °C 15.1: 8 mg / PTSA / dioxane; H2O / 24 h / 120 °C View Scheme

1: 542 mg / H2 / Pd/C / methanol / 1 h / 760 Torr 2: HMDS / CH2Cl2 / 1.25 h / -20 - 20 °C 3: 779 mg / tetrahydrofuran / 4 h / -78 - 20 °C 4: 60 percent / mCPBA / tetrahydrofuran / 1.5 h / -40 - 20 °C 5: 77 percent / toluene / 1 h / 70 °C 6: NaBH4 / ethanol / 5 h / 20 °C 7: 77 percent / DMAP / CH2Cl2 / 2 h / 20 °C 8: 83 percent / Bu3SnH; 1,1'-azobis(cyclohexanecarbonitrile) / toluene / 2 h / Heating 9: NaOMe / methanol / 24 h / 100 °C 10: 8 mg / PTSA / dioxane; H2O / 24 h / 120 °C View Scheme

in formic acid; water T=120°C; 12 h;

sodium tetrahydroborate in isopropyl alcohol T=20 - 50°C; 77 h; Inert atmosphere;

1: 77 percent / toluene / 1 h / 70 °C 2: NaBH4 / ethanol / 5 h / 20 °C 3: 77 percent / DMAP / CH2Cl2 / 2 h / 20 °C 4: 83 percent / Bu3SnH; 1,1'-azobis(cyclohexanecarbonitrile) / toluene / 2 h / Heating 5: NaOMe / methanol / 24 h / 100 °C 6: 8 mg / PTSA / dioxane; H2O / 24 h / 120 °C View Scheme

1: HMDS / CH2Cl2 / 1.25 h / -20 - 20 °C 2: 779 mg / tetrahydrofuran / 4 h / -78 - 20 °C 3: 60 percent / mCPBA / tetrahydrofuran / 1.5 h / -40 - 20 °C 4: 77 percent / toluene / 1 h / 70 °C 5: NaBH4 / ethanol / 5 h / 20 °C 6: 77 percent / DMAP / CH2Cl2 / 2 h / 20 °C 7: 83 percent / Bu3SnH; 1,1'-azobis(cyclohexanecarbonitrile) / toluene / 2 h / Heating 8: NaOMe / methanol / 24 h / 100 °C 9: 8 mg / PTSA / dioxane; H2O / 24 h / 120 °C View Scheme

1: NaOMe / methanol / 24 h / 100 °C 2: 8 mg / PTSA / dioxane; H2O / 24 h / 120 °C View Scheme