Table 1.
NMR Data (400 MHz, MeOH-d4) of Compounds 1 and 2.
1 | 2 | |||||
---|---|---|---|---|---|---|
position | δH, mult. (J in Hz) | δC, type | HMBCa | δH, mult. (J in Hz) | δC, type | HMBCa |
2 | 167.0, C | 161.8, C | ||||
3 | 6.28, s | 112.0, CH | 2, 4, 4a, 5, 1′ | 6.21, s | 107.3, CH | 2, 4, 4a, 5, 1′ |
4 | 179.4, C | 177.6, Cc | ||||
4a | 114.9, C | 112.9, C | ||||
5 | 136.8, C | 138.5, Cc | ||||
6 | 7.20, d (2.3) | 103.3, CH | 4a, 8, 5-COOH | 7.13, d (2.3) | 100.8, CH | 4a, 8, 5-COOH |
7 | 165.4, C | 163.4, C | ||||
8 | 7.22, d (2.3) | 116.8, CH | 4a, 6, 7, 8a | 7.20, d (2.3) | 114.0, CH | 4a, 7, 8a |
8a | 160.6, C | 157.9, C | ||||
1′a | 2.88, dd (4.1, 14.7) | 043.3, CH2 | 2, 3, 2′, 3′ | 6.33, dd (1.4, 15.6) | 121.5, CH | 2, 3′ |
1′b | 2.70, dd (9.2, 14.7) | 2, 3, 2′, 3′ | ||||
2′ | 4.06, m | 070.0, CH | 6.98, dt (7.3, 15.6) | 141.8, CH | 2, 3′, 4′ | |
3′ | 1.56, mb | 040.8, CH2 | 1′, 2′, 4′, 5′ | 2.31, ddt (1.4, 7.3, 7.3) | 034.0, CH2 | 1′, 2′, 4′, 5′ |
4′ | 1.56, mb / 1.45, m | 020.1, CH2 | 2′, 3′, 5′ | 1.58, sextet (7.3) | 020.9, CH2 | 2′, 3′, 5′ |
5′ | 0.98, t (6.9) | 014.5, CH3 | 3′, 4′ | 1.00, t (7.3) | 012.1, CH3 | 3′, 4′ |
7-OCH3 | 3.96, s | 057.1, CH3 | 7 | 3.95, s | 054.9, CH3 | 7 |
5-COOH | 171.9, C | 171.5, Cc |
HMBC correlations are from the proton(s) listed to the indicated carbons.
Overlapping signals
The quaternary 13C signals for C-4, C-5, and 5-COOH were very weak, and their δC values were corroborated by HMBC data.