lithium diisopropyl amide in tetrahydrofuran T=20°C; 3 h;

1: 95 percent / n-BuLi / 1 h / 20 °C 2: 85 percent / Dess-Martin periodinane 3: methanol 4: NaBH4 5: Et3N 6: 85 percent / LDA / tetrahydrofuran / 3 h / 20 °C View Scheme

1: methanol 2: NaBH4 3: Et3N 4: 85 percent / LDA / tetrahydrofuran / 3 h / 20 °C View Scheme

1: 85 percent / Dess-Martin periodinane 2: methanol 3: NaBH4 4: Et3N 5: 85 percent / LDA / tetrahydrofuran / 3 h / 20 °C View Scheme