Table 1.
1H NMR Spectroscopic Data (500 MHz, CDCl3) for Compounds 1–6
1a | 2a | 3a | 4a | 5b | 6a | |
---|---|---|---|---|---|---|
3 | 4.27, dd (4.0, 2.0) | 4.55, dd (5.0, 2.0) | 4.03, d (10.0) | 4.02, d (10.0) | 4.93, dd (8.5, 5.5) | 4.41, dd (12.5, 5.0) |
4 | 2.13, m | 2.33, m | 1.85, m | 1.85, m | 2.33, m | 2.30, m |
1.93, m | 1.88, m | 1.72, m | 1.71, m | 2.13, m | ||
5 | 2.82, ddd (19.0, 12.0, 7.0) | 3.40, m | 2.60, m | 2.60, m | 2.51, m | 2.71, m |
2.41, m | ||||||
2.40, dd (19.0, 7.0) | ||||||
7 | - | - | 3.13, s | 3.13, d (7.5) | 3.49, d (17.5) | - |
2.95, d (17.5) | ||||||
11 | - | - | - | - | - | 6.12, s |
13 | 6.07, s | 6.11, s | 6.12, s | 6.10, s | 6.35, s | - |
16 | 3.69, s | 3.68, s | 3.74, s | 3.73, s | 3.64, s | 3.74, s |
3′ | 7.53, br s | 7.54, br s | 7.59, br s | 7.54, d (1.5) | 7.38 d (2.0) | 7.53, br s |
5′ | 7.10, br s | 7.11, br s | 7.10, br s | 7.10, br s | 7.15 d (2.0) | 7.08, br s |
11′ | 4.93, d (7.5) | 4.96, d (7.5) | 4.79, d (7.5) | 4.92, d (7.5) | 4.59 d (7.0) | 5.21, d (7.5) |
12′ | 6.42, dd (8.5, 7.5) | 6.45, dd (8.5, 7.5) | 6.50, dd (8.5, 7.5) | 6.43, dd (8.5, 7.5) | 6.45, dd (8.5, 7.5) | 6.23, dd (8.5, 7.5) |
13′ | 7.01, d (8.5) | 7.02, d (8.5) | 6.69, d (8.5) | 7.02, dd (8.5, 1.0) | 6.81, d (8.5) | 7.05, d (8.5) |
15′ | 3.18, s | 3.20, s | 3.07, d (18.0) | 3.19, s | 3.12, s | 3.20, m |
2.91, d (18.0) | ||||||
16′ | 2.48, s | 2.49, s | 2.47, s | 2.48, s | 2.49, s | 2.46, s |
6-OH | 13.88, s | - | - | - | - | 13.94, s |
10-OH | 12.13, s | 12.18, s | 12.15, s | 12.29, s | 12.15, s | 11.17 s |
6′-OH | 10.68, s | 10.69, s | 11.71, s | 10.66, s | 10.51, s | 10.62, s |
9′-OH | nd | nd | nd | nd | 8.00, s | nd |
CDCl3.
DMSO-d6.