Table 2.
1H and 13C NMR spectroscopic data (CDCl3) for mammeasins E (2) and F (3).
| Position | 2aa | 2ba | 3ab | 3bb | ||||
|---|---|---|---|---|---|---|---|---|
| δH | δC | δH | δC | δH | δC | δH | δC | |
| 2 | 159.6 | 159.6 | 159.5 | 159.5 | ||||
| 3 | 6.61 (d, 0.9) | 107.0 | 6.59 (d, 1.0) | 107.1 | 6.62 (d, 1.0) | 107.1 | 6.61 (d, 1.0) | 107.2 |
| 4 | 160.7 | 160.7 | 160.6 | 1560.5 | ||||
| 4a | 101.0 | 101.1 | 101.0 | 101.2 | ||||
| 5 | 156.0 | 156.0 | 155.8 | 155.8 | ||||
| 6 | 105.8 | 106.0 | 105.9 | 106.1 | ||||
| 7 | 163.0 | 163.0 | 163.1 | 163.1 | ||||
| 8 | 104.5 | 104.6 | 104.3 | 104.3 | ||||
| 8a | 157.1 | 157.1 | 157.0 | 156.9 | ||||
| 1′ | 5.40 (br t, ca. 8) | 71.8 | 5.40 (br t, ca.8) | 71.7 | 5.43 (m) | 71.8 | 5.43 (m) | 71.8 |
| 2′ | 1.53, 1.96 (both m) | 30.7 | 1.53, 1.96 (both m) | 30.6 | 1.52, 1.96 (both m) | 30.7 | 1.52, 1.96 (both m) | 30.6 |
| 3′ | 1.12 (3H, t, 7.3) | 10.2 | 1.09 (3H, t, 7.1) | 10.1 | 1.12 (3H, t, 7.1) | 10.2 | 1.10 (3H, t, 7.1) | 10.1 |
| 2″ | 83.0 | 83.1 | 83.0 | 83.1 | ||||
| 3″ | 5.53 (d, 10.2) | 125.0 | 5.54 (d, 10.2) | 124.9 | 5.54 (d, 10.2) | 124.9 | 5.54 (d, 10.2) | 124.8 |
| 4″ | 6.79 (d, 10.2) | 116.5 | 6.78 (d, 10.2) | 116.5 | 6.79 (d, 10.2) | 116.6 | 6.79 (d, 10.2) | 116.6 |
| 5″ | 1.71, 1.90 (both m) | 41.6 | 1.71, 1.90 (both m) | 41.8 | 1.71, 1.91 (both m) | 41.7 | 1.71, 1.91 (both m) | 41.9 |
| 6″ | 2.08 (2H, m) | 23.0 | 2.08 (2H, m) | 23.2 | 2.09 (2H, m) | 23.0 | 2.09 (2H, m) | 23.3 |
| 7″ | 5.06 (qt, 1.0, 7.1) | 123.1 | 5.06 (qt, 1.0, 7.1) | 123.0 | 5.06 (dt, 1.3, 7.1) | 123.1 | 5.06 (qt, 1.3, 7.1) | 123.0 |
| 8″ | 132.6 | 132.5 | 132.6 | 132.6 | ||||
| 9″ | 1.64 (3H, d, 1.0) | 25.5 | 1.67 (3H, d, 1.0) | 25.6 | 1.64 (3H, br s) | 25.6 | 1.67 (3H, br s) | 25.6 |
| 10″ | 1.52 (3H, s) | 17.6 | 1.54 (3H, s) | 17.7 | 1.57 (3H, s) | 17.6 | 1.57 (3H, s) | 17.7 |
| 1‴ | 206.2 | 206.2 | 210.7 | 210.7 | ||||
| 2‴ | 3.14 (2H, d, 6.7) | 53.6 | 3.14 (2H, d, 6.7) | 53.6 | 3.89 (m) | 47.0 | 3.89 (m) | 47.0 |
| 3‴ | 2.27 (m) | 25.6 | 2.27 (m) | 25.5 | 1.25 (3H, d, 6.7) | 16.6 | 1.26 (3H, d, 6.7) | 16.6 |
| 4‴ | 1.03 (3H, d, 6.6) | 22.6 | 1.03 (3H, d, 6.6) | 22.6 | 1.46, 1.89 (both m) | 27.2 | 1.46, 1.89 (each m) | 27.2 |
| 5‴ | 1.03 (3H, d, 6.6) | 22.6 | 1.03 (3H, d, 6.6) | 22.6 | 0.98 (3H, t, 7.5) | 11.7 | 0.98 (3H, t, 7.5) | 11.7 |
| 2‴-CH3 | 1.51 (3H, s) | 27.3 | 1.48 (3H, s) | 27.5 | 1.52 (3H, br s) | 27.3 | 1.47 (3H, br s) | 27.5 |
| 7-OH | 14.51 (s) | 14.51 (s) | 14.44 (s) | 14.44 (s) | ||||
a
Measured by 700 MHz for 1H NMR and 175 MHz for 13C NMR.
b
Measured by 800 MHz for 1H NMR and 200 MHz for 13C NMR.