Supporting information for Kubanek et al. (2003) Proc. Natl. Acad. Sci. USA, 10.1073/pnas.1131855100
Table 2. NMR spectral data of lobophorolide (1) in CDCl3
C no. | Type | δ 13C | δ 1H | HMBC to: | COSY to: | 1D NOE or ROESY to: |
1 | C=O | 168.0 |
|
|
|
|
2 | HC=C | 118.0 | 5.85 d (J=15.5) | C1, 4 | H3 | H32 |
3 | HC=C | 150.5 | 7.54 d (J=16.0) | C1, 2, 5, 32 | H2 | H5 |
4 | C=C | 138.0 |
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|
|
|
5 | HC=C | 138.5 | 5.85 d (J=9.7) | C3, 32 | H6 | H3, 7 |
6 | CH | 71.1 | 4.28 dd (J=9.0, 9.0) | C4, 5, 7 | H5, 7 | H8a, 8b (w), 32 |
7 | CH | 82.4 | 3.44 m | C33 | H6, 8a, 8b (w) | H5, 9 |
8 | CH2 | 36.2 | 1.34 m 1.58 m |
| H7, 8b H7 (w), 8a, 9 | H6, 10 H6 (w), 13 |
9 | CH | 70.2 | 4.48 bd (J=10.0) |
| H8b, 10, 11 (w) | H7, 10, 33 |
10 | HC=C | 129.5 | 5.59 bd (J=10.0) | C9 (w) | H9, 11, 12b (w) | H8a, 9 |
11 | HC=C | 125.5 | 5.82 m |
| H9 (w), 10, 12a |
|
12 | CH2 | 31.4 | 1.92 m 2.00 m |
| H11, 13 H10 (w), 13 |
|
13 | CH | 66.8 | 3.28 m |
| H12a, 12b, 14a (LR), 14b | H8b, 15 |
14 | CH2 | 34.8 | 1.46 m 1.63 m | C15 (w) | H13 (LR), 14b, 15 H13, 14a, 15 | H35b H34 |
15 | CH | 78.3 | 3.87 dd (J=7.5, 3.0) | C13, 16, 17 | H14a, 14b | H13, 17, 34 |
16 | 4°C | 60.5 |
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|
|
|
17 | CH | 74.6 | 3.76 dd (J=10.5, 4.5) | C16 (w), 36 | H18a, 18b | H15, 19, 35a |
18 | CH2 | 27.5 | 1.40 m 1.92 m | C16 C16 | H17, 18b, 19 H17, 18a, 19 | H35a |
19 | CH | 77.2 | 3.21 m |
| H18a, 18b, 20 (LR) | H17, 20 |
20 | CH | 37.8 | 1.94 m | C21 | H19 (LR), 21, 38 | H19 |
21 | CH | 76.5 | 5.20 dd (J=10.5, 1.6) | C1, 38 | H20, 22 (LR) | H22, 37, 38 |
22 | CH | 37.6 | 1.92 m | C23 | H21 (LR), 23, 39 | H21 |
23 | CH | 76.1 | 3.01 dd (J=10.0, 2.0) |
| H22, 24 (LR) | H24, 39, 40 |
24 | CH | 33.0 | 1.70 m |
| H23 (LR), 25a, 40 | H23, 27, 39 |
25 | CH2 | 24.4 | 1.31 m 1.42 m |
| H24, 25b, 26b (w) H25a |
|
26 | CH2 | 29.4 | 1.26 m 1.91 m |
| H26b, 27 (w) H25a (w), 26a, 27 |
|
27 | CH | 71.8 | 4.00 m |
| H26a (w), 26b, 28a, 28b (w) | H24 |
28 | CH2 | 35.2 | 1.60 m 1.82 bd (J=13.0) | C26, 27, 29, 30 (w) | H27, 28b, 29 H27 (w), 28a, 29 |
|
29 | CH | 73.5 | 3.52 m | C41 | H28a, 28b, 30a, 30b |
|
30 | CH2 | 39.1 | 1.14 m 1.97 m | C28, 29 (w), 31, 42 | H29, 30b H29, 30a, 31 (w) | H42 |
31 | CH | 64.6 | 3.68 m |
| H30b (w), 42 |
|
32 | Me | 12.8 | 1.89 s (3H) | C3, 4, 5 |
| H2, 6 |
33 | OMe | 61.0 | 3.62 s (3H) | C7 |
| H9 |
34 | OMe | 57.8 | 3.43 s (3H) | C15 |
| H14b, 15 |
35 | CH2 | 45.2 | 2.62 d(J=4.0) 2.64 d(J=4.5) | C16, 17 C16, 17 | H35b H35a | H17, 18a H14a |
36 | OMe | 53.1 | 3.19 s (3H) | C17 |
|
|
37 | OMe | 58.6 | 3.21 s (3H) | C19 |
| H21 |
38 | Me | 9.3 | 0.84 d (3H, J=7.0) | C19, 20, 21 | H20 | H21 |
39 | Me | 9.2 | 0.81 d (3H, J=7.0) | C21, 22, 23 | H22 | H23, 24 |
40 | Me | 18.2 | 1.01 d (3H, J=6.5) | C23, 24, 25 | H24 | H23 |
41 | OMe | 55.7 | 3.32 s (3H) | C29 |
|
|
42 | Me | 22.0 | 1.18 d (3H, J=6.0) | C29 (w), 30, 31 | H31 | H30b |
HMBC, heteronuclear multiple-bond correlation; NOE, nuclear Overhauser effect; ROESY, rotating frame Overhauser effect spectroscopy; LR, long range; w, weak.