phenyllithium 1.) ether, THF, 0.75 h, RT; 2.) THF, ether, RT, overnight; Yield given. Multistep reaction;

1.1: NaN3 / dimethylformamide / 2 h / 50 °C 1.2: 69 percent / EtONa / -30 °C 2.1: 87 percent / aq. HCl / tetrahydrofuran / 20 °C 3.1: 96 percent / P(OMe)3 / benzene / 20 °C 4.1: 39 percent / DIBALH / CH2Cl2 / -78 °C View Scheme

1.1: NaN3 / dimethylformamide / 2 h / 50 °C 1.2: 69 percent / EtONa / -30 °C 2.1: 87 percent / aq. HCl / tetrahydrofuran / 20 °C 3.1: 96 percent / P(OMe)3 / benzene / 20 °C 4.1: Me3Al / tetrahydrofuran; toluene / 0.5 h / 20 °C 4.2: 87 percent / tetrahydrofuran; toluene / 3 h / 20 °C 5.1: 96 percent / tetrahydrofuran; diethyl ether / -40 °C View Scheme

1.1: NaN3 / dimethylformamide / 2 h / 50 °C 1.2: 69 percent / EtONa / -30 °C 2.1: 87 percent / aq. HCl / tetrahydrofuran / 20 °C 3.1: 96 percent / P(OMe)3 / benzene / 20 °C View Scheme

1: 75 percent / sodium ethoxide / ethanol / 0.17 h / Ambient temperature 2: 83 percent / 3M hydrochloric acid / 24 h View Scheme

1.1: NaN3 / dimethylformamide / 2 h / 50 °C 1.2: 69 percent / EtONa / -30 °C 2.1: 87 percent / aq. HCl / tetrahydrofuran / 20 °C 3.1: 96 percent / P(OMe)3 / benzene / 20 °C 4.1: 85 percent / NaBH4; CaCl2 / tetrahydrofuran; ethanol / 0.75 h / -20 °C View Scheme

1: dichloromethane / 15 h / 20 °C / |Inert atmosphere 2: 2-mesityl-2,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]triazol-4-ium chloride; triethylamine / toluene / 10 h / 25 °C View Scheme

1: 2) acid 2: 91 percent / (EtO)3P / benzene / 21 h / Ambient temperature View Scheme

1: (1S,2R)-N,N-dibutylnorephedrine <(1S,2R)-DBNE> / hexane / 17 h / Ambient temperature 2: 1.) H+, 2.) silver oxide / 1.) hydrolysis, 2.) oxidation View Scheme