1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: tetrahydrofuran; hexane / 1 h / -78 °C 2.1: DCC; 4-(dimethylamino)pyridine / CH2Cl2 / 20 °C 3.1: Candida rugosa lipase; MgCl2 / H2O; diisopropyl ether / 24 h / 30 °C 4.1: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 5.1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 6.1: DEAD; PPh3 / diethyl ether; toluene / 30 h / -10 °C 6.2: 78 percent / diethyl ether; toluene / 2.5 h / -10 °C 7.1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C 8.1: 99 percent / HCl / diethyl ether View Scheme

1.1: DEAD; PPh3 / diethyl ether; toluene / 30 h / -10 °C 1.2: 78 percent / diethyl ether; toluene / 2.5 h / -10 °C 2.1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C 3.1: 99 percent / HCl / diethyl ether View Scheme

1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C 2: 99 percent / HCl / diethyl ether View Scheme

1: NaHCO3 / tetrahydrofuran 2: LiAlH4 / tetrahydrofuran / Heating 3: 1) DEAD, Ph3P View Scheme

1: 78 percent / H2O 2: 98 percent / LiAlH4 / diethyl ether 3: 95 percent / CH2Cl2 4: Ph3P, DEAD / diethyl ether 5: 89 percent / HCl / ethanol View Scheme

triphenylphosphine; diethylazodicarboxylate Yield given. Multistep reaction;