1: 77 percent / Na / liquid ammonia 2: 91 percent / NaBH4 View Scheme

Multi-step reaction with 6 steps 1: 77 percent / LiCl, p-benzoquinone / Pd(OAc)2 (7percent) / acetic acid2: 77 percent / acetonitrile; dimethylsulfoxide / 3 h / 80 °C3: 98 percent / H2 / RhCl(PPh3)3 / ethanol / 15 h / 20 °C / 4560 Torr4: 99 percent / NaOH / methanol; H2O5: 100 percent / Et3N / tetrahydrofuran6: 97 percent / K2CO3 / methanol / 1 h / 20 °C  

Multi-step reaction with 5 steps 1: 77 percent / acetonitrile; dimethylsulfoxide / 3 h / 80 °C2: 98 percent / H2 / RhCl(PPh3)3 / ethanol / 15 h / 20 °C / 4560 Torr3: 99 percent / NaOH / methanol; H2O4: 100 percent / Et3N / tetrahydrofuran5: 97 percent / K2CO3 / methanol / 1 h / 20 °C  

Multi-step reaction with 4 steps 1: 98 percent / H2 / RhCl(PPh3)3 / ethanol / 15 h / 20 °C / 4560 Torr2: 99 percent / NaOH / methanol; H2O3: 100 percent / Et3N / tetrahydrofuran4: 97 percent / K2CO3 / methanol / 1 h / 20 °C