Reaction Steps
To a solution of COMPOUND 307 (273 mg, 0.522 mmol) in MeOH (5 mL) cooled to −15° C. was added a solution of OXONE® (1.41 g, 2.30 mmol) in H2O (5 mL) and the mixture was stirred at −15° C. for 15 minutes. Standard work-up and purification afforded COMPOUND 308 as a white solid (69 mg, 23%). 1H NMR (CDCl3) δ 0.96-1.25 (m, 2H), 1.03 (d, 3H, J=6.6 Hz), 1.54-1.61 (m, 1H), 1.71-1.84 (m, 3H), 2.21 (t, 1H, J=10.2 Hz), 2.53 (s, 6H), 2.60 (t, 1H, J=11.1 Hz), 2.77-2.92 (m, 3H), 2.99 (s, 3H), 3.31-3.38 (m, 1H), 3.66-3.74 (m, 1H), 3.82-3.89 (m, 1H), 3.98 (s, 2H), 6.67 (d, 2H, J=9.0 Hz), 6.98-7.01 (m, 2H), 7.32 (dd, 1H, J=5.1, 3.0 Hz), 7.66 (d, 2H, J=9.0 Hz), 8.49-8.50 (m, 1H), 8.92 (s, 1H). 13C NMR (CDCl3) δ 13.85, 22.35, 29.53, 30.67, 31.23, 40.34, 43.92, 45.40, 45.54, 52.25, 55.99, 60.54, 112.25, 121.23, 126.45, 126.93, 129.57, 130.66, 131.26, 139.96, 152.59, 157.99, 163.51, 166.72. ES-MS m/z 556 (M+H). Anal. Calcd. for C28H37N5O3S2.0.6H2O: C, 59.36; H, 6.80; N, 12.36; S, 11.32. Found: C, 59.38; H, 6.74; N, 12.07; S, 11.22.
