Table 2.
NMR Spectroscopic Dataa for 974-B (2), PFF-B (4) and fucodiphlorethol G (5, part) in CD3OD.
| 974-B (2) | PFF-B (4) | ||||||||
|---|---|---|---|---|---|---|---|---|---|
| ring | position | δC | δH (mult, J) | HMBC b | δC | δH (mult, J) | ΔδC (2–4) | ||
| A | 1′ | 159.0 | 161.8 | −2.9 | |||||
| 2′ | 102.5 | 95.1 | 5.97 (d,205) | 7.3 | |||||
| 3′ | 156.9 | 159.9 | −3.1 | ||||||
| 4′ | 98.4 | 6.20 (d,2.05) | 2′,3′,5′,6′ | 97.2 | 5.92 (t,2.05) | 1.1 | |||
| 5′ | 159.6 | 159.9 | −0.4 | ||||||
| 6′ | 95.2 | 6.15 (d,2.05) | 1′,2′,4′,5′ | 95.1 | 5.97 (d 2.05) | 0.0 | |||
| B | 1 | 124.0 | 124.3 | −0.4 | |||||
| 2 | 147.0 | 147.5 | −0.6 | ||||||
| 3 | 99.6 | 6.17 (s) | 1,2,4,4a,15a | 99.2 | 6.16 (s) | 0.3 | |||
| 4 | 143.9 | 143.5 | 0.3 | ||||||
| 4a | 125.3 | 125.2 | 0.0 | ||||||
| 15a | 138.0 | ND c | ND c | ||||||
| C | 5a | 142.9 | 143.0 | −0.2 | |||||
| 6 | 92.7 | 6.69 (s) | 5a,6a,13,14,14a | 92.0 | 6.66 (s) | 0.6 | |||
| 6a | 152.7 | 152.3 | 0.3 | ||||||
| 13 | 109.9 | 109.7 | 0.1 | ||||||
| 14 | 138.3 | 138.2 | 0.0 | ||||||
| 14a | 127.4 | 127.6 | −0.3 | ||||||
| D | 7a | 150.9 | 150.7 | 0.1 | |||||
| 8 | 122.1 | 122.2 | −0.2 | ||||||
| 9 | 151.6 | 151.3 | 0.2 | ||||||
| 10 | 99.5 | 6.38 (s) | 7a,8,9,11,12,13 | 98.9 | 6.37 (s) | 0.5 | |||
| 11 | 148.4 | 147.6 | 0.7 | ||||||
| 12 | 106.4 | 106.7 | −0.4 | ||||||
| E | 1″ | 161.9 | 161.7 | 0.1 | |||||
| 2″,6″ | 95.3 | 5.87 (d,2.06) | 1″,3″,4″(H2″) | 94.9 | 5.87 (d,2.03) | 0.3 | |||
| 3″,5″ | 160.2 | 160.0 | 0.1 | ||||||
| 4″ | 97.6 | 5.91 (t,2.05) | 2″,3″,5″,6″ | 97.2 | 5.94 (t,2.05) | 0.3 | |||
| fucodiphlorethol G (5, part) [17] | |||||||||
| ring | position | δC | δH (mult, J) | ΔδC (2–5) | |||||
| F | 1′′′ | 159.2 | D | 1″ | 159.4 | −0.2 | |||
| 2′′′ | 102.7 | 2″ | 102.0 | 0.7 | |||||
| 3′′′ | 157.5 | 3″ | 159.2 | −1.7 | |||||
| 4′′′ | 98.6 | 6.22 (d, 2.06) | 2′′′,3′′′,5′′′,6′′′ | 4″ | 97.5 | 6.10 (d, 2.2) | 1.1 | ||
| 5′′′ | 159.7 | 5″ | 159.5 | 0.2 | |||||
| 6′′′ | 94.2 | 5.89 (d, 2.05) | 1′′′,2′′′,4′′′,5′′′ | 6″ | 94.3 | 6.03 (d, 2.2) | −0.1 | ||
| G | 1″″ | 124.7 | A | 1 | 124.9 | −0.2 | |||
| 2″″ | 152.2 | 2 | 152.0 | 0.2 | |||||
| 3″″ | 97.6 | 6.05 (d, 2.64) | 1″″,2″″,4″″,5″″ | 3 | 98.0 | 6.02 d (d, 2.7) | −0.4 | ||
| 4″″ | 156.6 | 4 | 157.5 | 0.9 | |||||
| 5″″ | 94.2 | 5.75 (d, 2.64) | 1″″,3″″,4″″,6″″ | 5 | 94.5 | 5.69 d (d, 2.7) | −0.3 | ||
| 6″″ | 153.8 | 6 | 153.7 | 0.1 | |||||
| H | 1′′′′′ | 124.0 | B | 1′ | 124.3 | −0.3 | |||
| 2′′′′′,6′′′′′ | 152.2 | 2′,6′ | 152.1 | 0.1 | |||||
| 3′′′′′,5′′′′′ | 96.5 | 6.00 (s) | 1′′′′′,2′′′′′,4′′′′′(H3′′′′′) | 3′,5′ | 96.0 | 5.91 (s) | 0.5 | ||
| 4′′′′′ | 156.5 | 4′ | 157.9 | −1.4 | |||||
a 1H NMR (600 MHz), 13C NMR (151 MHz), chemical shift (ppm), J (Hz), the signals of CHD2OD (δH 3.30) and 13CD3OD (δC 49.0) were used as internal references; b Correlations are from proton to carbon; c ND denotes not determined; d In ref. [17], the signals were oppositely assigned.