1: LiAlH4 2: MnO2 3: SnCl4 4: HF 5: NaOMe 6: ion exchange resin Dowex 50W-X8(H+) 7: 42 percent / NaOMe View Scheme

1: 98 percent / HF; pyridine 2: 45 percent / (BrC6H4)3NSbCl6 / CH2Cl2 / 0.33 h / 20 °C 3: lutidine 4: LiAlH4 5: MnO2 6: NaOMe 7: Dowex 50W-X8 (H+) 8: 56 percent / NaOMe 9: 54 percent / TBAF; AcOH / 50 °C View Scheme