Reaction Steps
colorless amorphous solid; [α]22D −3 (c 1.5, MeOH); UV (MeOH) λmax nm (ε) 211 (15800), 248 (11900); IR (KBr) νmax 3435, 2963, 2931, 2878, 1731, 1706, 1457, 1273, 979 cm−1; 1H NMR (CDCl3, 600 MHz) δ 6.99 (1H, s, H-19), 6.57 (1H, bs, H17), 5.56*(1H, ddd, J=15.1, 7.4, 7.0 Hz, H-12), 5.41 (1H, ddd, J=15.1, 7.0, 6.9 Hz, H-13), 5.41 (1H, dd, J=7.7, 2.8 Hz, H-15), 4.13 (1H, dddd, J=6.7, 6.2, 5.6, 5.1 Hz, H-3), 3.78 (1H, ddd, J=8.2, 6.5, 1.9 Hz, H-7), 3.18 (1H, d, J=5.6 Hz, 3-OH), 3.06 (1H, dq, J=8.2, 7.1 Hz, H-6),2.98 (1H, dq, J=6.2, 7.0 Hz, H-4), 2.71 (3H, s, H-21),2.64 (1H, dd, J=15.1, 6.7 Hz, H2a), 2.54 (1H, dd, J=15.1, 5.1 Hz, H-2b), 2.44 (2H, m, H-14),2.22 (1H, dddd, J=13.8, 7.0, 6.2, 2.9 Hz, H-11a), 2.10 (3H, d, J=1.1 Hz, H-27), 2.09 (˜H, d, J=6.5 Hz, 7-OH), 1.88 (1H, dddd, J=13.8, 10.9, 7.4, 2.9 Hz, H-11b), 1.65 (1H, m, H-8), 1.63 (1H, m, H-10a), 1.56 (1H, dddd, J=12.7, 12.7, 3.9, 3.9 Hz, H-9a), 1.20 (3H, d, J=7.1 Hz, H-24), 1.15 (3H, d, J=7.0 Hz, H-23),1.13 (1H, m, H-10b), 1.04 (1H, m, H-9.b), 1.01 (3H, d, J=7.0 Hz, H-25); 13C NMR, see Table 1; EIMS m/z 463 [M]+ (13), 290 (11), 190 (10), 168 (100), 164 (20), 157 (26), 139 (17); HREIMS m/z 463.2383 (calcd. for C25H37NO5S, 463.2392).
