1: 1) disiamylborane, 2) HOAc / 1) THF, 0 deg C, 1h, 2) RT, 4h 2: 71 percent / 3N HCl / methanol / 1.5 h / Ambient temperature 3: 88 percent / pyridine / acetonitrile / 1 h / 0 °C 4: 43 percent / t-BuOOH, D-(-)-DIPT, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH2Cl2 / 16 h / -21 °C 5: t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / -21 °C 6: PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C 7: 1N NaOH / methanol / 1 h / 0 °C 8: 1) Bu3SnLi, 2) I2 / 1) THF, 0 deg C, 3h, 2) Et2O, 0 deg C 9: imidazole / dimethylformamide / Ambient temperature 10: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 11: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 71 percent / 3N HCl / methanol / 1.5 h / Ambient temperature 2: 88 percent / pyridine / acetonitrile / 1 h / 0 °C 3: 43 percent / t-BuOOH, D-(-)-DIPT, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH2Cl2 / 16 h / -21 °C 4: t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / -21 °C 5: PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C 6: 1N NaOH / methanol / 1 h / 0 °C 7: 1) Bu3SnLi, 2) I2 / 1) THF, 0 deg C, 3h, 2) Et2O, 0 deg C 8: imidazole / dimethylformamide / Ambient temperature 9: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 10: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 43 percent / t-BuOOH, D-(-)-DIPT, Ti(O-i-Pr)4, molecular sieves 4 Angstroem / CH2Cl2 / 16 h / -21 °C 2: t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / -21 °C 3: PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C 4: 1N NaOH / methanol / 1 h / 0 °C 5: 1) Bu3SnLi, 2) I2 / 1) THF, 0 deg C, 3h, 2) Et2O, 0 deg C 6: imidazole / dimethylformamide / Ambient temperature 7: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 8: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

2: 43 percent / t-BuOOH, Ti(O-i-Pr)4, D-(-)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 21 h / -21 °C 3: Br2 / CH2Cl2 / 0.17 h / -70 °C 4: n-Bu4NF / tetrahydrofuran / 0.25 h / -70 °C 5: imidazole / dimethylformamide / 5 h / Ambient temperature 6: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature 7: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min 8: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 9: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: imidazole / dimethylformamide / 5 h / Ambient temperature 2: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature 3: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min 4: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 5: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: imidazole / dimethylformamide / Ambient temperature 2: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 3: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature 2: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min 3: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 4: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 2: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 2: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

1: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min 2: 1) disiamylborane, 2) LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h, 2) 40 degC, 12h 3: 79 percent / n-Bu4NF / tetrahydrofuran / 18 h / Ambient temperature View Scheme