Table 1.
NMR data (700 MHz, CD3OD) for swinholides A (1) and J (2) (δ in ppm, J in Hz).
|
1a |
2a |
|||||
|---|---|---|---|---|---|---|
| Position | Type | δH/δH′ (J in Hz) | δC/δC′ | δH/δH′ (J in Hz) | δC/δC′ | HMBCb |
| 1/1′ | C | - | 170.6 | - | 170.2/168.7 | |
| 2/2′ | CH | 5.84 d (15.7) | 115.6 | 5.90 d (15.6)/6.14 d (15.7) | 115.9/122.2 | C1, C4 |
| C1′, C4′ | ||||||
| 3/3′ | CH | 7.43 d (15.7) | 152.3 | 7.46 d (15.6)/6.82 d (15.7) | 152.0/152.4 | C1, C5 |
| C1′ | ||||||
| 4/4′ | C | - | 135.5 | - | 135.5/59.7 | |
| 4/4′-Me | CH3 | 1.77 s | 12.4 | 1.85 s/1.42 s | 12.7/15.5 | C3, C4, C5 |
| C3′, C4′, C5′ | ||||||
| 5/5′ | CH | 6.14 t (7.3) | 140.5 | 6.16 t (7.2)/3.22 dd (4.3, 7.4) | 140.6/64.6 | C3, 4-Me |
| 6/6′ | CH2 | 2.40 t (6.9) | 38.8 | 2.44 m/1.81 m, 1.63 m | 38.7/37.9 | C4, C5, C7, C8 |
| 7/7′ | CH | 4.02 m | 68.1 | 3.99 ovl/4.12 m | 68.2/66.5 | |
| 8/8′ | CH2 | 1.28 m | 41.0 | 1.87 m, 1.37 m/ | 41.8/41.6 | |
| 1.76 m | 1.78 m, 1.37 m | |||||
| 9/9′ | CH | 4.47 br d (10.5) | 70.5 | 4.48 br d (10.2) | 70.4 | |
| 10/10′ | CH | 5.65 dd (1.8, 10.5) | 130.9 | 5.67 br d (10.3) | 130.8 | |
| 11/11′ | CH | 5.81 m | 124.9 | 5.83 m | 124.8 | |
| 12/12′ | CH2 | 1.94 m | 32.2 | 1.96 m | 32.2 | |
| 13/13′ | CH | 3.49 m | 65.3 | 3.54 m | 65.4 | |
| 14/14′ | CH2 | 1.58 m | 37.2 | 1.58 m | 36.9 | |
| 1.77 m | 1.82 m | |||||
| 15/15′ | CH | 3.76 m | 78.2 | 3.76 m/3.83 m | 78.4/77.9 | |
| 15/15′-OMe | CH3 | 3.32 s | 56.7 | 3.34 s/3.35 s | 56.9/57.2 | C15/C15′ |
| 16/16′ | CH | 1.52 m | 43.8 | 1.55 m | 43.3 | |
| 16/16′-Me | CH3 | 0.83 d (6.7) | 8.8 | 0.83 d (7.0)/0.84 d (7.0) | 9.2 | C15, C16, C17 |
| C15′, C16′, C17′ | ||||||
| 17/17′ | CH | 3.61 m | 73.2 | 3.60 m | 73.2 | |
| 18/18′ | CH2 | 1.63 m | 39.0 | 1.61 m | 39.2 | |
| 1.74 m | 1.75 m | |||||
| 19/19′ | CH | 3.97 ovl | 70.1 | 3.97 ovl/3.88 m | 70.0/70.1 | |
| 20/20′ | CH | 1.94 m | 39.4 | 1.94 m | 39.4 | |
| 20/20′-Me | CH3 | 0.91 d (7.0) | 8.9 | 0.90 d (7.1)/0.91 d (7.1) | 9.1 | |
| 21/21′ | CH | 5.46 d (10.5) | 75.6 | 5.45 t (10.3)/5.46 t (10.3) | 75.7/76.3 | |
| 22/22′ | CH | 1.98 m | 37.9 | 1.97 m | 38.0 | |
| 22/22′-Me | CH3 | 0.94 d (6.9) | 9.6 | 0.92 d (7.0)/0.93 d (7.0) | 9.7 | C21, C22, C23 |
| C21′, C22′, C23′ | ||||||
| 23/23′ | CH | 3.11 dd (1.8, 9.5) | 77.2 | 3.10 m | 77.3 | |
| 24/24′ | CH | 1.70 m | 34.4 | 1.70 m | 34.5 | |
| 24/24′-Me | CH3 | 0.98 d (6.7) | 17.7 | 0.97 d (6.7)/0.98 d (6.7) | 17.9 | C23, C24, C25 |
| C23′, C24′, C25′ | ||||||
| 25/25′ | CH2 | 1.24 m | 25.1 | 1.23 m, 1.41 m | 25.1 | |
| 1.42 m | ||||||
| 26/26′ | CH2 | 1.27 m | 29.7 | 1.28 m, 1.94 m | 29.8 | |
| 1.94 m | ||||||
| 27/27′ | CH | 3.99 ovl | 72.7 | 3.98 ovl | 72.8 | |
| 28/28′ | CH2 | 1.52 m | 35.8 | 1.52 m | 35.8 | |
| 1.87 br d (12.8) | 1.87 br d (12.5) | |||||
| 29/29′ | CH | 3.61 m | 74.2 | 3.61 m | 74.3 | C29-OMe |
| C29′-OMe | ||||||
| 29/29′-OMe | CH3 | 3.34 s | 55.3 | 3.34 s | 55.3 | C29 |
| C29′ | ||||||
| 30/30′ | CH2 | 1.09 dd (10.4, 12.6) | 39.7 | 1.09 dd (10.4, 12.6) | 39.7 | |
| 2.01 br d (12.6) | 2.02 br d (12.6) | |||||
| 31/31′ | CH | 3.74 m | 65.7 | 3.74 m | 65.8 | |
| 31/31′-Me | CH3 | 1.19 d (6.2) | 21.8 | 1.19 d (6.2) | 21.8 | |
a
Data from COSY, HSQC, and HMBC experiments;
b
HMBC correlations, optimized for 6 Hz, are from proton(s) stated to the indicated carbon.