1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 2: 83 percent / pyridine / 3 h / 0 °C 3: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 4: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 5: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 6: NaBH4 / methanol / 24 h / 20 °C View Scheme

1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 2: 83 percent / pyridine / 3 h / 0 °C 3: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 4: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 5: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 6: NaBH4 / methanol / 24 h / 20 °C 7: 46.3 mg / 48 h / Heating 8: 94 percent / lithium aluminum hydride / tetrahydrofuran / 7 h / 20 °C View Scheme