samarium diiodide; water; triethylamine in tetrahydrofuran T=23°C; 18 h; Inert atmosphere; chemoselective reaction;

1: 1.) diisopropylethylamine, dibutylboryl triflate (n-Bu2BOTf), 2.) N-bromosuccinimide (NBS) / 1.) CH2Cl2, a.) -78 deg C, 15 min, b.) 0 deg C, 1 h, 2.) -78 deg C, 1.25 h 2: tetramethylguanidinium azide (TMGA) / CH2Cl2 / 1.) 0 deg C, 0.5 h, 2.) 25 deg C, 1.0 h 3: 97 percent / lithium hydroxide / tetrahydrofuran; H2O / 0.5 h / 0 °C 4: 97 percent / H2 / 10percent Pd/C / H2O; acetic acid / 1 h / 7757.2 Torr View Scheme

1: 82 percent / NaN(SiMe3)2 / tetrahydrofuran / 2.5 h / -78 °C 2: 91 percent / H2O2; LiOH / tetrahydrofuran; H2O / 1 h / 0 °C View Scheme

hydroxylamine hydrochloride; triethylamine; Sm(OTf)3 in tetrahydrofuran T=20°C; 72 h;

1: 1.) sodium hexamethyldisilylamide / 1.) THF, -65 deg C, 45 min, 2.) THF, -70 deg C, 3 h 2: 1.) n-butyllithium / 1.) THF, hexane, -5 deg C, 2.) THF, hexane, 0 deg C, 3 h 3: 92.5 percent / trifluoroacetic acid / CH2Cl2 / Ambient temperature View Scheme

1: 1.) sodium hexamethyldisilylamide / 1.) THF, -65 deg C, 45 min, 2.) THF, -70 deg C, 3 h 2: 1.) n-butyllithium / 1.) THF, hexane, -5 deg C, 2.) THF, hexane, 0 deg C, 3 h View Scheme