Table 1. NMR Data for Chaetoglobosin-510 (1), -540 (2), and -542 (3) in MeOHa.
| position | δC | δH (J in Hz) | gHMBCb | δC | δH (J in Hz) | gHMBCb | δC | δH (J in Hz) | gHMBCb |
|---|---|---|---|---|---|---|---|---|---|
| 1 | 176.6(C) | 173.7(C) | 175.7(C) | ||||||
| 3 | 59.3 (CH) | 3.35 (dd, 7.0, 2.5) | 1, 3′, 5, 9, 10 | 58.6 (CH) | 3.35 (t, 3.5) | 59.2 (CH) | 3.40 (dd, 6.5, 2.0,) | 1, 3′, 4, 10 | |
| 4 | 45.9 (CH) | 2.95 (dd, 5.5, 2.0) | 1, 5, 6, 9, 10, 23 | 44.3 (CH) | 3.25 (dd, 5.0, 3.5) | 46.6 (CH) | 2.86 (dd, 5.5, 2.0) | 1, 3, 5, 10, 23 | |
| 5 | 42.9 (CH) | 2.03 (m) | 4,6,7, 11 | 42.8 (CH) | 2.08 (m) | 3.1 (CH) | 2.08 (m) | ||
| 6 | 138.7(C) | 140.6(C) | 138.6(C) | ||||||
| 7 | 127.7 (CH) | 5.30 (m) | 125.9 (CH) | 5.28 (m) | 126.7 (CH) | 5.35 (m) | |||
| 8 | 46.2 (CH) | 2.80 (m) | 7, 13 | 47.0 (CH) | 2.55 (m) | 46.5 (CH) | 2.88 (m)c | 6, 9 | |
| 9 | 67.1(C) | 66.9(C) | 67.5(C) | ||||||
| 10 | 36.6 (CH) | 2.88 (p, 7.0) | 2′, 3, 3′, 3a′, 10′ | 35.8 (CH) | 3.10 (dq, 7.5, 3.5) | 10′ | 36.8 (CH) | 2.89 (p, 7.0) | 3′ |
| 10′ | 15.1 (CH3) | 1.22 (d, 7.0) | 3, 3′, 10 | 13.8 (CH3) | 1.20 (d, 7.5) | 3′, 3 | 15.6 (CH3) | 1.24 (d, 7.5) | 3′, 3, 10 |
| 11 | 20.4 (CH2) | 1.18 (m) | 5, 6, 11′ | 21.0 (CH2) | 1.60 (m) | 11′ | 20.5 (CH2) | 1.20 (m) | 11′ |
| 1.69 (m) | 5, 11′ | 1.90 (m) | 11′ | 1.78 (m) | 11′ | ||||
| 11′ | 11.9 (CH3) | 0.70 (t, 7.2) | 5, 11 | 12.2 (CH3) | 1.10 (t, 7.0) | 5, 11 | 12.0 (CH3) | 0.68 (t, 7.0) | 5, 11 |
| 12 | 18.2 (CH3) | 1.71 (d, 1.5) | 5,6,7 | 18.5 (CH3) | 1.80 (d, 1.5) | 5, 6, 7 | 18.2 (CH3) | 1.72 (br s) | 6, 7 |
| 13 | 128.5 (CH) | 6.09 (ddd, 15.0, 10.0, 2.0) | 130.7 (CH) | 5.94 (ddd, 15.0, 10.0, 1.5) | 128.4 (CH) | 6.00 (ddd, 15.5, 9.0, 1.5) | |||
| 14 | 133.2 (CH) | 5.12 (ddd, 15.0, 10.0, 3.0) | 15 | 130.8 (CH) | 5.08 (ddd, 15.0, 11.0, 4.0) | 133.4 (CH) | 5.12 (ddd, 15.5, 9.5, 3.0) | ||
| 15 | 40.0 (CH2) | 1.79 (m) | 17 | 41.7 (CH2) | 1.90 (m) | 16 | 39.9 (CH2) | 1.74 (m) | |
| 2.23 (m) | 17 | 2.21 (ddd, 13.5, 4.0, 3.5) | 2.18 (m) | ||||||
| 16 | 33.0 (CH) | 2.49 (m) | 31.8 (CH) | 2.43 (m) | 31.8 (CH) | 2.50 (m) | |||
| 16′ | 20.5 (CH3) | 0.9 (d, 6.6) | 15, 16, 17 | 19.8 (CH3) | 0.90 (d, 7.0) | 15, 16, 17 | 20.2 (CH3) | 0.90 (d, 6.5) | 15, 16 |
| 17 | 132.6 (CH) | 4.78 (dq, 10.0, 1.5) | 16, 19 | 139.9 (CH) | 5.51 (dq, 9.0, 1.5) | 19 | 134.1 (CH) | 4.80 (m)c | 19 |
| 18 | 130.8 (C) | 132.5(C) | 132.9(C) | ||||||
| 18′ | 15.1 (CH3) | 1.54 (d, 1.5) | 17 | 9.3 (CH3) | 1.30 (d, 1.5) | 17, 18, 19 | 12.0 (CH3) | 1.64 (d, 1.0) | 18, 19 |
| 19 | 37.0 (CH2) | 2.20 (m) | 18, 21 | 81.2 (CH) | 4.99 (s) | 17, 18, 18′, 20 | 79.2 (CH) | 4.05 (d, 3.5) | |
| 20 | 28.9 (CH2) | 2.32 (m) | 18, 21, 22 | 200.7(C) | 75.3 (CH) | 4.47 (ddd, 5.0, 3.5, 1.5) | |||
| 21 | 146.6 (CH) | 6.72 (dt, 15.5, 7.5) | 20, 22,23 | 131.0 (CH) | 6.20 (d, 17.0) | 19, 22, 23 | 146.1 (CH) | 6.65 (dd, 15.5, 5.0) | 20 |
| 22 | 126.8 (CH) | 6.58 (d, 15.5) | 20, 21 | 136.3 (CH) | 7.60 (d, 17.0) | 20,23 | 125.1 (CH) | 6.32 (dd, 15.5, 2.0) | 1 |
| 23 | 198.8(C) | 198.5 (C) | 199.5 (C) | ||||||
| 2′ | 121.8 (CH) | 6.97 (s) | 7a′, 2′,3a′ | 121.0 (CH) | 6.95 (s) | 3′ | 118.4 (CH) | 6.95 (s) | 3′, 7a′ |
| 3′ | 116.0(C) | 115.4(C) | 116.2(C) | ||||||
| 3a′ | 126.2(C) | 126.3(C) | 126.7(C) | ||||||
| 4′ | 118.3 (CH) | 7.42 (dt, 8.0, 1.0) | 7a′, 3a′, 5′, 6′ | 118.4 (CH) | 7.45 (dd, 8.0, 1.0) | 7a′, 5′ | 118.3 (CH) | 7.42 (brd, 8.0) | 6′, 7a′ |
| 5′ | 118.3 (CH) | 6.92 (ddd, 8.0, 7.0, 1.0) | 6′, 7′ | 122.3 (CH) | 6.94 (ddd, 8.0, 7.0, 1.0) | 3a′ | 122.0 (CH) | 6.96 (ddd, 8.0, 7.0, 1.0) | |
| 6′ | 120.9 (CH) | 7.05 (ddd, 8.0, 7.0, 1.0) | 7a′, 5′ | 118.4 (CH) | 6.96 (ddd, 8.0, 7.0, 1.0) | 7a′ | 120.9 (CH) | 7.15 (ddd, 8.0, 7.0, 1.0) | 7a′ |
| 7′ | 111.0 (CH) | 7.30 (dt, 8.0, 1.0) | 5′, 6′ | 111.2 (CH) | 7.20 (dd, 8.0, 1.0) | 6′ | 110.0 (CH) | 7.30 (brd, 8.0) | 2′ |
| 7a′ | 136.7 (C) | 136.9 (C) | 136.7 (C) |
a
Measured at 500 MHz (1H) and 125.7 MHz (13C).
b
Denotes proton correlating to carbon.
c
Determined by gCOSY and gHMBC correlation.