Reaction Steps
To a solution of tert-butyl((3S,7R,8R,9S)-7-(2-bromoethyl)-9-methyl-2-oxo-8-phenoxyoxonan-3-yl)carbamate (408 mg, 0.867 mmol) and AIBN (14.24 mg, 0.087 mmol) in anhydrous toluene (8.7 mL) was added Bu3SnH (257 μl, 0.954 mmol), and the reaction was heated to 80° C. After 1 h, TLC (4:1 hexanes: acetone) still showed starting material. An additional 0.5 equivalents of Bu3SnH and 0.05 equiv AIBN were added and the reaction was stirred for an additional 1 h at 80° C. The reaction was cooled to room temperature, stirred with 10% aqueous potassium fluoride (KF) solution (7 mL) for 20 h, and partitioned between Et2O (20 mL) and sat. NaCl solution (20 mL). The phases were separated and the aqueous phase was extracted with Et2O (2×20 mL). The organic extracts were combined, dried over MgSO4, filtered and concentrated to provide a white solid, which was purified by column chromatography on SiO2 (5→20% acetone/hexanes) to provide the title compound as a white solid (295 mg, 87%): 1H NMR (400 MHz, CDCl3) δ 7.38-7.16 (m, 2H), 7.00-6.87 (m, 3H), 5.19-4.97 (m, 2H), 4.18 (t, J=8.8 Hz, 2H), 2.27 (dt, J=13.1, 6.7 Hz, 1H), 1.91-1.77 (m, 1H), 1.70-1.58 (m, 3H), 1.58-1.48 (m, 1H), 1.44 (s, 9H), 1.28 (d, J=6.5 Hz, 3H), 1.25-1.14 (m, 2H), 1.12-1.01 (m, 1H), 0.86 (t, J=7.3 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 173.34, 159.68, 154.91, 129.58, 120.95, 115.40, 81.44, 79.86, 74.74, 53.00, 44.96, 34.20, 28.34, 27.85, 27.03, 26.85, 23.50, 18.74, 18.40, 17.53, 13.61, 11.86; ESIMS m/z 392.3 ([M+H]+), 414.3 ([M+Na]+).
