Table 1.
NMR spectroscopic data (500 MHz, CD3OD) for phocoenamicins B (1) and C (2).
| Position | Phocoenamicin B (1) | Phocoenamicin C (2) | ||
|---|---|---|---|---|
| δC, Type | δH, Mult. (J in Hz) | δC, Type | δH, Mult. (J in Hz) | |
| 1 | 178.1, C a | 172.7, C a | ||
| 2 | 107.4, C | n.d * | ||
| 3 | 201.3, C a | 176.2, C | ||
| 4 | 51.2, C | 47.1, C | ||
| 5 | 43.9, CH | 1.85, m | 44.1, CH | 1.60, m |
| 6 | 39.6, CH | 1.42, m | 38.6, CH | 1.52, m |
| 7α | 46.0, CH2 | 1.70, m | 46.0, CH2 | 1.75, m |
| 7β | 1.20, m | 1.11, m | ||
| 8 | 40.9, CH | 1.60, m | 40.8, CH | 1.63, m |
| 9 | 88.9, CH | 3.03, t (9.2) | 88.0, CH | 3.03, t (9.8) |
| 10 | 48.4, CH | 1.93, m | 48.3, CH | 1.92, m |
| 11 | 126.4, CH | 6.22, d (10.4) | 126.4, CH | 6.27, dd (10.3, 2.5) |
| 12 | 127.9, CH | 5.55, dd (9.8, 5.9) | 128.2, CH | 5.63, ddd (10.3, 6.2, 2.4) |
| 13 | 42.1, CH | 2.72, m | 50.6, CH | 2.00, m |
| 14 | 39.8, CH | 2.10, m | 40.7, CH | 2.21, m |
| 15 | 141.5, CH | 5.27, m | 136.3, CH | 4.90, m |
| 16 | 123.7, CH | 5.18, dd (15.2, 11.8) | 129.3, CH | 5.27, ddd (15.7, 11.6, 3.1) |
| 17a | 44.1, CH2 | 2.34, m | 43.1, CH2 | 2.32, m |
| 17b | 1.85, m | 1.70, m | ||
| 18 | 41.1, C | 44.3, C | ||
| 19 | 133.6, CH | 5.26, s | 133.5, CH | 4.99, brs |
| 20 | 138.0, C | 134.8, C | ||
| 21 | 30.1, CH | 2.58, m | 34.6, CH | 2.33, m |
| 22α | 30.5, CH2 | 1.68, m | 29.8, CH2 | 1.73, m |
| 22β | 2.26, m | 2.38, m | ||
| 23 | 87.1, C | 87.0, C | ||
| 24 | 204.4, C a | n.d * | ||
| 25 | 16.8, CH3 | 1.53, s | 17.3, CH3 | 1.31, s |
| 26 | 24.0, CH3 | 0.80, brs | 22.1, CH3 | 0.93, d (6.8) |
| 27 | 20.2, CH3 | 1.02, d (6.2) | 20.0, CH3 | 1.02, d (6.4) |
| 28 | 21.5, CH3 | 0.80, brs | 22.5, CH3 | 0.89, d (7.2) |
| 29 | 24.6, CH3 | 1.23, brs | 23.7, CH3 | 1.26, s |
| 30a | 65.4, CH2 | 4.14, d (13.2) | 22.4, CH3 | 1.73, s |
| 30b | 3.98, d (13.2) | |||
| 31a | 33.5, CH2 | 2.07, m | 33.9, CH2 | 1.94, m |
| 31b | 1.69, m | 1.73, m | ||
| 32 | 74.1, CH | 3.86, dd (11.2, 1.4) | 74.1, CH | 3.84, dd (10.9, 1.9) |
| 33 | 83.5, C | 83.5, C | ||
| 34 | 215.3, C | 215.2, C | ||
| 35 | 25.7, CH3 | 2.24, s | 25.6, CH3 | 2.23, s |
| 36 | 22.2, CH3 | 1.24, s | 22.1, CH3 | 1.20, s |
| 1′ | 104.0, CH | 4.36, d (7.3) | 104.0, CH | 4.35, d (7.3) |
| 2′ | 75.4, CH | 3.45, m | 75.4, CH | 3.45, m |
| 3′ | 88.6, CH | 3.46, m | 88.6, CH | 3.48, m |
| 4′ | 75.7, CH | 3.11, t (8.8) | 75.6, CH | 3.11, t (8.8) |
| 5′ | 72.8, CH | 3.22, m | 72.9, CH | 3.24, m |
| 6′ | 18.3, CH3 | 1.27, d (6.0) | 18.3, CH3 | 1.28, d (6.0) |
| 1″ | 105.4, CH | 4.61, d (7.8) | 105.4, CH | 4.61, d (7.9) |
| 2″ | 76.1, CH | 3.42, t (8.5) | 76.1, CH | 3.42, t (8.6) |
| 3″ | 75.3, CH | 3.64, t (9.3) | 75.4, CH | 3.64, t (9.4) |
| 4″ | 77.9, CH | 4.89, ** | 77.9, CH | 4.87, ** |
| 5″ | 71.7, CH | 3.69, dq (9.7, 6.1) | 71.7, CH | 3.69, dq (9.7, 6.2) |
| 6″ | 18.0, CH3 | 1.35, d (6.1) | 18.0, CH3 | 1.35, d (6.2) |
| 1′′′ | 124.3, C | 124.3, C | ||
| 2′′′ | 135.6, C | 135.6, C | ||
| 3′′′ | 126.0, C | 126.0, C | ||
| 4′′′ | 132.4, CH | 7.25, d (8.7) | 132.4, CH | 7.25, d (8.7) |
| 5′′′ | 115.9, CH | 6.70, d (8.7) | 115.8, CH | 6.70, d (8.7) |
| 6′′′ | 155.3, C | 155.3, C | ||
| 7′′′ | 169.3, C | 169.3, C | ||
| 37 | 17.3, CH3 | 2.36, s | 17.9, CH3 | 2.36, s |
a Assigned based on 2D correlations. * n.d. = not detected; ** Obscured by the water peak.