Table 1.
NMR Spectroscopic Data (500 MHz, CDCl3) for (+)-Dioxosarcoguaiacol (2)
| position | δCa | mult. | δH (J in Hz) | HMBCb | NOESYc |
|---|---|---|---|---|---|
| 1 | 145.8 | C | |||
| 2 | 35.6 | CH2 | H-2a: 2.58, ddd (16.7, 8.5, 7.2) H-2b: 2.21, ddd (16.7, 10.9, 0) |
H-2a ↔ H-3b, 15 | |
| 3 | 29.9 | CH2 | H-3a: 1.95, m H-3b: 1.40, dddd (16.6, 8.5, 3.5, 0) |
H-3a ↔ 4 H-3b ↔ H-2a, 14 |
|
| 4 | 44.3 | CH | 2.63, m | ||
| 5 | 132.5 | C | |||
| 6 | 114.6 | CH | 5.55, s | C-11, 4, 8, 7, 5 | H-13, 12, 14, 4 |
| 7 | 153.2 | C | |||
| 8 | 103.4 | C | |||
| 8-OH | 3.08, br s | ||||
| 9 | 38.0 | CH2 | H-9a: 1.63, dd (13.4, 13.4) H-9b: 2.03, dd (13.4, 5.2) |
C-14, 10, 8, 7, 1 | H-9a ↔ H-15 H-9b ↔ H-15 |
| 10 | 31.5 | CH | 2.71, m | ||
| 11 | 85.3 | C | |||
| 12 | 28.0 | CH3 | 1.37, s | C-15, 11, 7 | H-6 |
| 13 | 24.8 | CH3 | 1.43, s | C-12, 11, 7 | H-6 |
| 14 | 20.1 | CH3 | 1.04, d (7.1) | C-3, 4, 5 | |
| 15 | 19.6 | CH3 | 1.12, d (7.1) | C-10, 9, 8, 1 | H-9a, 9b, 2a |
a
13C shifts are deduced from HSQC and HMBC experiments.
b
HMBC correlations from hmbcgp experiment (NS: 128, DS: 16), optimized for 10 Hz, are from proton(s) stated to the indicated carbon.
c
Critical NOESY correlations from noesygpphpp experiment (mixing time 0.75 s, NS: 32, DS: 16)