1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C 2: formic acid; triethylamine / Ru(η6-mesitylene)-(R,R)-TsDPEN / CH2Cl2 / 20 °C 3: NBS; H2O; NaHCO3 / NaOAc*3H2O / tetrahydrofuran / 0 °C 4: DMAP / CH2Cl2 / -78 °C 5: Pd2(DBA)3*CHCl3; triphenylphosphine / CH2Cl2 / 0 - 20 °C 6: NaBH4 / CH2Cl2; methanol / -78 °C 7: pyridine; DMAP / CH2Cl2 / 20 °C 8: TMSN3 / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 50 °C 9: TBAF / tetrahydrofuran / 20 °C 10: triethylamine / CH2Cl2 11: N-methylmorpholine N-oxide; water / OsO4 / 2-methyl-propan-2-ol; acetone 12: H2 / Pd(OH)2/C / ethanol / 20 °C / 5171.48 Torr View Scheme

Multi-step reaction with 8 steps 1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C2: formic acid; triethylamine / Ru(η6-mesitylene)-(R,R)-TsDPEN / CH2Cl2 / 20 °C3: NBS; H2O; NaHCO3 / NaOAc*3H2O / tetrahydrofuran / 0 °C4: DMAP / CH2Cl2 / -78 °C5: Pd2(DBA)3*CHCl3; triphenylphosphine / CH2Cl2 / 0 - 20 °C6: NaBH4 / CH2Cl2; methanol / -78 °C7: pyridine; DMAP / CH2Cl2 / 20 °C8: TMSN3 / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 50 °C  

Multi-step reaction with 3 steps 1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C2: formic acid; triethylamine / Ru(η6-mesitylene)-(R,R)-TsDPEN / CH2Cl2 / 20 °C3: NBS; H2O; NaHCO3 / NaOAc*3H2O / tetrahydrofuran / 0 °C  

Multi-step reaction with 5 steps 1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C2: formic acid; triethylamine / Ru(η6-mesitylene)-(R,R)-TsDPEN / CH2Cl2 / 20 °C3: NBS; H2O; NaHCO3 / NaOAc*3H2O / tetrahydrofuran / 0 °C4: DMAP / CH2Cl2 / -78 °C5: Pd2(DBA)3*CHCl3; triphenylphosphine / CH2Cl2 / 0 - 20 °C  

Multi-step reaction with 10 steps 1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C2: formic acid; triethylamine / Ru(η6-mesitylene)-(R,R)-TsDPEN / CH2Cl2 / 20 °C3: NBS; H2O; NaHCO3 / NaOAc*3H2O / tetrahydrofuran / 0 °C4: DMAP / CH2Cl2 / -78 °C5: Pd2(DBA)3*CHCl3; triphenylphosphine / CH2Cl2 / 0 - 20 °C6: NaBH4 / CH2Cl2; methanol / -78 °C7: pyridine; DMAP / CH2Cl2 / 20 °C8: TMSN3 / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 50 °C9: N-methylmorpholine N-oxide; water / OsO4 / 2-methyl-propan-2-ol; acetone10: para-toluenesulfonic acid monohydrate / acetone / 0 °C  

Multi-step reaction with 7 steps 1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C2: formic acid; triethylamine / Ru(η6-mesitylene)-(R,R)-TsDPEN / CH2Cl2 / 20 °C3: NBS; H2O; NaHCO3 / NaOAc*3H2O / tetrahydrofuran / 0 °C4: DMAP / CH2Cl2 / -78 °C5: Pd2(DBA)3*CHCl3; triphenylphosphine / CH2Cl2 / 0 - 20 °C6: NaBH4 / CH2Cl2; methanol / -78 °C7: pyridine; DMAP / CH2Cl2 / 20 °C  

Multi-step reaction with 9 steps 1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C2: formic acid; triethylamine / Ru(η6-mesitylene)-(R,R)-TsDPEN / CH2Cl2 / 20 °C3: NBS; H2O; NaHCO3 / NaOAc*3H2O / tetrahydrofuran / 0 °C4: DMAP / CH2Cl2 / -78 °C5: Pd2(DBA)3*CHCl3; triphenylphosphine / CH2Cl2 / 0 - 20 °C6: NaBH4 / CH2Cl2; methanol / -78 °C7: pyridine; DMAP / CH2Cl2 / 20 °C8: TMSN3 / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 50 °C9: N-methylmorpholine N-oxide; water / OsO4 / 2-methyl-propan-2-ol; acetone  

Multi-step reaction with 9 steps 1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C2: formic acid; triethylamine / Ru(η6-mesitylene)-(R,R)-TsDPEN / CH2Cl2 / 20 °C3: NBS; H2O; NaHCO3 / NaOAc*3H2O / tetrahydrofuran / 0 °C4: DMAP / CH2Cl2 / -78 °C5: Pd2(DBA)3*CHCl3; triphenylphosphine / CH2Cl2 / 0 - 20 °C6: NaBH4 / CH2Cl2; methanol / -78 °C7: pyridine; DMAP / CH2Cl2 / 20 °C8: TMSN3 / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 50 °C9: TBAF / tetrahydrofuran / 20 °C  

Multi-step reaction with 10 steps 1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C2: formic acid; triethylamine / Ru(η6-mesitylene)-(R,R)-TsDPEN / CH2Cl2 / 20 °C3: NBS; H2O; NaHCO3 / NaOAc*3H2O / tetrahydrofuran / 0 °C4: DMAP / CH2Cl2 / -78 °C5: Pd2(DBA)3*CHCl3; triphenylphosphine / CH2Cl2 / 0 - 20 °C6: NaBH4 / CH2Cl2; methanol / -78 °C7: pyridine; DMAP / CH2Cl2 / 20 °C8: TMSN3 / allylpalladium chloride dimer; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 50 °C9: TBAF / tetrahydrofuran / 20 °C10: triethylamine / CH2Cl2  

Multi-step reaction with 4 steps 1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C2: formic acid; triethylamine / Ru(η6-mesitylene)-(R,R)-TsDPEN / CH2Cl2 / 20 °C3: NBS; H2O; NaHCO3 / NaOAc*3H2O / tetrahydrofuran / 0 °C4: DMAP / CH2Cl2 / -78 °C