1: 88 percent / NaH / dimethylformamide 2: 89 percent / NaBH4 / methanol 3: Et3N / CH2Cl2 / 1.5 h 4: NaBH4 / dimethylformamide 5: K2CO3 / methanol 6: O3, Me2S / CH2Cl2; pyridine / -78 °C 7: CrO3, acid / acetone / -30 °C 8: ethyl acetate View Scheme

1: 88 percent / NaH / dimethylformamide 2: 89 percent / NaBH4 / methanol 3: Et3N / CH2Cl2 / 1.5 h 4: NaBH4 / dimethylformamide 5: K2CO3 / methanol 6: O3, Me2S / CH2Cl2; pyridine / -78 °C 7: CrO3, acid / acetone / -30 °C 8: ethyl acetate 9: 86 percent / BCl3 / CH2Cl2 / 192 h View Scheme

1: 88 percent / NaH / dimethylformamide 2: 89 percent / NaBH4 / methanol 3: Et3N / CH2Cl2 / 1.5 h 4: NaBH4 / dimethylformamide 5: K2CO3 / methanol 6: O3, Me2S / CH2Cl2; pyridine / -78 °C 7: CrO3, acid / acetone / -30 °C 8: ethyl acetate 9: 86 percent / BCl3 / CH2Cl2 / 192 h 10: LiOH / H2O View Scheme