1: 1.) disiamylborane, 2.) aq. 2N NaOH, Pd(PPh3)4 / 1.) THF,0 deg C, 1h; 2.) 50 deg C, 16 h 2: 80 percent / nBu4NF / tetrahydrofuran / 18 h / 25 °C View Scheme

1: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh3)4 / 1) THF, 0 deg C, 1h 2: 55 percent / n-Bu4NF / tetrahydrofuran / 12 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

With  potassium cyanide; silver nitrate in  tetrahydrofuran; ethanol; water T=0°C;   

Multi-step reaction with 3 steps 1: imidazole / dimethylformamide / 0 - 20 °C2: 94 percent / Pd(PPh3)4, CuI, nPrNH2 / benzene / 20 °C3: 90 percent / KCN, AgNO3, / ethanol; tetrahydrofuran; H2O / 0 °C  

Multi-step reaction with 2 steps 1: 94 percent / Pd(PPh3)4, CuI, nPrNH2 / benzene / 20 °C2: 90 percent / KCN, AgNO3, / ethanol; tetrahydrofuran; H2O / 0 °C  

Multi-step reaction with 5 steps 1: Br2 / CH2Cl2 / 0 °C2: nBu4NF / tetrahydrofuran / 0 °C3: imidazole / dimethylformamide / 0 - 20 °C4: 94 percent / Pd(PPh3)4, CuI, nPrNH2 / benzene / 20 °C5: 90 percent / KCN, AgNO3, / ethanol; tetrahydrofuran; H2O / 0 °C  

Multi-step reaction with 6 steps 1: 43 percent / t-BuOOH, Ti(O-i-Pr)4, D-(-)-DIPT, molecular sieves 4 Angstroem / CH2Cl2 / 21 h / -21 °C2: Br2 / CH2Cl2 / 0.17 h / -70 °C3: n-Bu4NF / tetrahydrofuran / 0.25 h / -70 °C4: imidazole / dimethylformamide / 5 h / Ambient temperature5: n-PrNH2 / Pd(PPh3)4, CuI / benzene / 20 h / Ambient temperature6: 1) AgNO3, 2) KCN / 1) THF, EtOH, H2O, 0 deg C, 30 min, 2) 0 deg C, 30 min