Table 4.
1H NMR (400 MHz) data for 4′-hydroxy-gilvocarcin E (5), 4′-hydroxy-gilvocarcin M (6), 12-demethyl-defucogilvocarcin V (8) and defucogilvocarcin V (7, for comparison) in [D6]DMSO (relative to internal TMS, J in Hz).
| Position | Multiplicity | |||
|---|---|---|---|---|
| 5 | 6 | 8 | 7 | |
| 1-OH | 9.70, s | 9.70, s | ** | 9.54, s |
| 2 | 6.91, d (8) | 6.90, d (8) | 6.80, dd (7.5, 1) | 6.98, dd (8.4, 1.2) |
| 3 | 8.04, d (8) | 8.04, d (8) | 7.44, t (7.5) | 7.53, t (8.4) |
| 4 | 7.83, dd (7.5, 1) | 7.90, dd (8.4, 1.2) | ||
| 7 | 7.80, d (1.6) | 7.79, br s | 8.0, d (1.2) | 8.02, d (1.5) |
| 9 | 7.53, d (1.6) | 7.51, br s | 7.71, d (1.2) | 7.74, d (1.5) |
| 10-OCH3 | 4.13, s | 4.12, s | 4.12, s | 4.17, s |
| 11 | 8.49, s | 8.48, s | 8.23, s | 8.40, s |
| 12-OH | ** | |||
| 12-OCH3 | 4.12, s | 4.12, s | 4.11, s | |
| 13-H | 2.82, q (8) | 2.5, s* | 6.92, dd (11.4, 17.4) | 6.93, dd (11.4, 17.4) |
| 14-H | 1.29, t (8) | He 6.13, d (17.4) | He 6.15, d (17.4) | |
| Hz 5.48, d (11.4) | Hz 5.50, d (11.4) | |||
| 1′ | 6.34, d (6.8) | 6.33, d (6.4) | – | – |
| 2′ | 4.85, dd (6.8, 6.8) | 4.84, dd (6.8, 6.4) | – | – |
| 2′-OH | 4.51, d (6.8) | 4.50, d (6.8) | – | – |
| 3′ | 3.92, t (6.8) | 3.92, t (6.8) | – | – |
| 3′-OH | 4.91, d (6.8) | 4.92, d (6.8) | – | – |
| 4′-OH | 5.25, s | 5.24, s | – | – |
| 5′ | 3.72, dq (6.4, 5.2) | 3.72, dq (6.4, 5.2) | – | – |
| 5′-OH | 4.87, d (5.2) | 4.86, d (5.2) | – | – |
| 6′-CH3 | 1.24, d (6.4) | 1.25, d (6.4) | – | – |
*
Signal obscured by solvent
**
not observed signals because of overlap with H2O