Table 1.
NMR Data for Precandidaspongiolides A (1) and B (2) and Candidaspongiolides A (3) and B (4) (600 MHz, CD3OD)
| precandidaspongiolide A (1) | precandidaspongiolide B (2) | candidaspongiolide A (3) | candidaspongiolide B (4) | |||||
|---|---|---|---|---|---|---|---|---|
| no. | δC | δH, mult (J, Hz) | δC | δH, mult (J, Hz) | δC | δH, mult (J, Hz) | δC | δH, mult (J, Hz) |
| 1 | 173.4 | — | 173.3 | — | 173.2 | — | 173.1 | — |
| 2 | 73.1 | 3.76a (2.0) | 72.7 | 3.60, d (1.9) | 73.0 | 3.77, d (1.9) | 72.7 | 3.57, d (1.9) |
| 3 | 84.8 | 3.81, dd (9.5, 2.0) | 84.9 | 3.66, dd (9.5, 1.9) | 85.4 | 3.80, dd (9.4, 1.9) | 85.1 | 3.68, dd (9.8, 1.9) |
| 4 | 49.6 | 3.15,a (9.5, 7.1) | 48.5 | 3.34, dq (9.5, 7.2) | 48.9 | 3.21, dq (9.4, 7.0) | 48.2 | 3.31,d (9.8, 6.9) |
| 5 | 217.8 | — | 217.2 | — | 216.1 | — | 215.4 | — |
| 6 | 51.3 | 3.15,a (10.0, 7.0) | 51.6 | 3.15, dq (10.2, 6.9) | 50.0 | 3.41, dq (10.2, 7.1) | 49.7 | 3.35,c (6.7) |
| 7 | 80.0 | 4.04, d (10.0) | 79.2 | 4.15, d (10.2) | 81.4 | 5.39, d (10.2) | 81.3 | 5.48,c |
| 8 | 139.1 | — | 135.8 | — | 134.7 | — | 131.4 | — |
| 9 | 129.9 | 5.33, br d (9.5)b | 132.5 | 5.40, br d (10.0) | 133.3 | 5.45, br d (9.8) | 135.9 | 5.55 br d (10.0) |
| 10 | 46.7 | 3.38, dq (9.5, 6.8) | 44.3 | 2.35, dq (10.0, 6.9) | 46.6 | 3.35, dq (9.8, 6.8) | 44.6 | 2.32, dq (10.0, 6.8) |
| 11 | 212.9 | — | 100.5 | — | 212.2 | — | 100.4 | — |
| 12a | 44.4 | 2.75, dd (17.6, 9.6) | 41.1 | 2.01, dd (13.6, 4.3) | 44.5 | 2.70, dd (17.6, 9.6) | 41.2 | 1.99, dd (13.8, 4.2) |
| 12b | 2.24, dd (17.6, 1.7) | 1.03,c (13.6, 12.7) | 2.24, dd (17.6, 1.9) | 1.00,c (13.8, 12.6) | ||||
| 13 | 69.5 | 4.44, dd (9.6, 1.7) | 71.9 | 4.22, dd (12.7, 4.3) | 69.4 | 4.46, dd (9.6, 1.9) | 71.9 | 4.21, dd (12.6, 4.2) |
| 14 | 85.4 | — | 79.1 | — | 85.5 | — | 79.1 | — |
| 15 | 216.6 | — | 212.1 | — | 216.5 | — | 212.1 | — |
| 16 | 48.9 | 4.08, ddd (11.2, 10.8, 4.1) | 51.9 | 4.36,c (11.7, 10.4, 3.8) | 49.0 | 4.04, ddd (11.0, 10.7, 3.9) | 52.0 | 4.35,c (11.9, 10.4, 3.9) |
| 17 | 78.5 | 3.21, d (10.8) | 78.9 | 3.02, d (10.4) | 78.4 | 3.23, d (10.7) | 78.9 | 3.00, d (10.4) |
| 18 | 64.1 | — | 63.9 | — | 63.7 | — | 63.8 | — |
| 19 | 67.5 | 2.64, d (9.4) | 67.3 | 2.66, d (9.2)b | 67.5 | 2.64, d (9.2) | 67.3 | 2.62, d (9.2) |
| 20 | 32.6 | 2.48, ddq (10.7, 9.4, 6.6) | 32.6 | 2.64,c (9.2, 7.2) | 32.5 | 2.48, ddq (10.7, 9.2, 6.5) | 32.5 | 2.50,c |
| 21 | 131.8 | 5.33, ddq (10.9, 10.7, 1.5)b | 132.0 | 5.32,c (1.6) | 131.8 | 5.35, ddq (10.9, 10.7, 1.5) | 132.0 | 5.32, ddq (10.9, 10.6, 1.4) |
| 22 | 126.3 | 5.51, dq (10.9, 6.8) | 126.1 | 5.50,c (6.9) | 126.3 | 5.51, dq (10.9, 6.7) | 126.1 | 5.50,c (6.8) |
| 23 | 13.7 | 1.63, dd (6.8, 1.5) | 13.7 | 1.60, dd (6.9, 1.6) | 13.7 | 1.63, dd (6.7, 1.5) | 13.7 | 1.60, dd (6.8, 1.5) |
| 24 | 15.2 | 1.23, d (7.1) | 15.5 | 1.25, d (7.2)b | 15.0 | 1.23, d (7.0) | 15.6 | 1.15, d (6.9) |
| 25 | 15.7 | 1.26, d (7.0) | 15.2 | 1.14, d (6.9) | 14.8 | 1.18, d (7.1) | 14.5 | 1.13, d (6.7) |
| 26 | 10.5 | 1.66, br s | 10.4 | 1.51, br s | 11.0 | 1.66, br s | 10.6 | 1.50, br s |
| 27 | 15.8 | 1.04, d (6.8) | 13.0 | 0.95, d (6.9) | 15.6 | 1.00, d (6.8) | 12.8 | 0.91, d (6.8) |
| 28a | 65.8 | 3.75,a s | 66.8 | 3.63, d (11.2) | 65.8 | 3.75, s | 66.8 | 3.62, d (11.2) |
| 28b | — | 3.53, d (11.2) | — | 3.53, d (11.2) | ||||
| 29a | 65.3 | 4.34, dd (10.8, 4.1) | 65.4 | 4.31, dd (11.7, 10.0) | 65.0 | 4.33, dd (10.8, 3.9) | 65.4 | 4.31, dd (11.9, 10.0) |
| 29b | 3.93, dd (11.2, 10.8) | 3.98, dd (10.0, 3.8) | 3.95, dd (11.0, 10.8) | 3.98, dd (10.0, 3.9) | ||||
| 30 | 11.6 | 1.35, s | 11.5 | 1.38, s | 11.6 | 1.35, s | 11.5 | 1.35, s |
| 31 | 18.8 | 1.11, d (6.6) | 18.9 | 1.12, d (7.2)b | 18.9 | 1.10, d (6.5) | 18.9 | 1.10, d (6.5) |
| 32 | 61.5 | 3.39, s | 61.2 | 3.31, s | 61.5 | 3.41, s | 61.3 | 3.32, s |
| 33 | 171.9 | — | 172.0 | — | ||||
| 34 | 21.0 | 2.03, s | 21.0 | 2.03, s | ||||
a
Signals overlapped.
b
Measured in d6-acetone.
c
Signal obscurred by major/minor isomer.
d
Buried under CD3OD signal.