| Spirornata A | Spirornata B | Spirornata C | ||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
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CN: Carbon number in the structures. a NMR spectra recorded using Bruker AVANCE III 500 MHz (AV 500) spectrometer (Bruker, Karlsruhe, Germany) in deuteriated chloroform (CDCl) as aprotic 3 solvent at ambient temperature with tetramethyl silane (TMS) as the internal standard (δ 0 ppm). NMR data was administered using MestReNova-7.1.1–9649. 1 H NMR spectra were recorded at 500 MHz, while the 13 C NMR spectra were recorded at 125 MHz. |
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| C. | 13C | δ 1H NMR (mult., J | COSY | HMBC | C. | 13C | δ 1H NMR (mult., | COSY | HMBC | C. | 13C | δ 1H NMR (mult., | COSY | HMBC |
| N. | in Hz, int)b | N. | J in Hz, int)b | N. | J in Hz, int)b | |||||||||
| 2 | 62.1 | 4.02 (Ha) (1H, d, J | H-2a | C-7 | 2 | 61.6 | 4.05 (Ha) (1H, d, | – | C-2a, 8 | 2 | 62.4 | 4.09 (Ha) (1H, d, | – | C-2a, 8 |
| = 9.65) | J = 8.65) | J = 7.86) | ||||||||||||
| 3.83 (Hb) (1H, d, J | 3.37 (Hb) (1H, d, | 3.48 (Hb) (1H, d, | ||||||||||||
| = 8.85) | J = 8.55) | J = 7.68) | ||||||||||||
| 2a | 42.6 | 2.82 (1H, t, J = | – | C-3, 5a | 2a | 127.9 | – | – | – | 2a | 127.9 | – | – | – |
| 7.99) | ||||||||||||||
| 3 | 179.2 | – | – | – | 3 | 47.2 | 2.90 (2H, s) | – | C-2a, 4 | 3 | 48.1 | 2.96 (2H, s) | C-2a, 4 | |
| 5 | 70.4 | 4.38 (Ha) (1H, d, J | H-5a | C-3 | 4 | 203.5 | – | – | – | 4 | 202.4 | – | – | – |
| = 8.65) | ||||||||||||||
| 4.12 (Hb) (1H, d, J | ||||||||||||||
| = 8.56) | ||||||||||||||
| 5a | 35.2 | 2.32 (1H, t, J = | H-6 | C-5 | 5 | 39.7 | 2.48 (2H, dd, J = | H-6 | C-4, 6a | 5 | 40.8 | 2.46 (2H, dd, J = | H-6 | C-4, 6a |
| 7.99) | 10.19, 4.86) | 10.34, 4.76) | ||||||||||||
| 6 | 37.7 | 2.18 (1H, m) | H-8 | C-5a, 7 | 6 | 22.5 | 2.27 (2H, dd, J = | – | C-4, 6a | 6 | 25.5 | 2.24 (2H, dd, J = | – | C-4, 6a |
| 10.09, 4.66) | 10.33, 4.96) | |||||||||||||
| 7 | 101.4 | – | – | – | 6a | 125.7 | – | – | – | 6a | 124.7 | – | – | – |
| 8 | 14.2 | 1.02 (3H, d, J = | – | C-6 | 7 | 72.5 | 5.53 (1H, s) | – | C-6a, 8, | 7 | 41.1 | 2.36 (Ha) (1H, d, | – | C-6a, 8 |
| 7.22) | 9 | J = 4.65) | ||||||||||||
| 2.07 (Hb) (1H, d, | ||||||||||||||
| J = 5.15) | ||||||||||||||
| 3 ʹ | 41.2 | 2.42 (1H, m) | H-4 ʹ | C-7, 1 a, | 8 | 98.6 | – | – | – | 8 | 97.8 | – | – | – |
| 2 a | ||||||||||||||
| 4 ʹ | 27.7 | 1.67 (1H, m) | C-5 ʹ | 9 | 170.9 | – | – | – | 3 ʹ | 41.7 | 2.99 (1H, d, J = | H-4 ʹ | C-8, 1 a | |
| 7.46) | ||||||||||||||
| 5 ʹ | 43.1 | 1.52 (Ha) (1H, dd, J | H-6 ʹ | C-6 ʹ | 10 | 21.2 | 2.23 (3H, s) | – | C-9 | 4 ʹ | 71.4 | 5.42 (1H, dt, | H-5 ʹ | C-5 ʹ, 8 ʹ |
| = 10.09, 4.96) | 5.22, 7.44) | |||||||||||||
| 1.46 (Hb) (1H, dd, J | ||||||||||||||
| = 10.09, 4.66) | ||||||||||||||
| 6 ʹ | 68.5 | 3.75 (1H, m) | H-7 ʹ | C-7 | 3 ʹ | 35.6 | 2.37 (1H, m) | H-4 ʹ | C-8, 1 a, | 5 ʹ | 35.6 | 1.92 (Ha) (1H, m) | H-6 ʹ | C-6 ʹ |
| 2 a | 1.65 (Hb) (1H, m) | |||||||||||||
| 7 ʹ | 22.8 | 1.11 (3H, d, J = | – | C-6 ʹ | 4 ʹ | 23.4 | 1.72 (Ha) (1H, m) | H-5 ʹ | C-3 ʹ | 6 ʹ | 68.2 | 3.75 (1H, m) | H-7 ʹ | C-8 |
| 5.45) | 1.38 (Hb) (1H, m) | |||||||||||||
| 8 ʹ | 19.3 | 0.96 (3H, d, J = | – | C-4 ʹ | 5 ʹ | 29.5 | 1.51 (Ha) (1H, m) | H-6 ʹ | – | 7 ʹ | 21.9 | 1.20 (3H, d, J = | – | C-6 ʹ |
| 6.79) | 1.45 (Hb) (1H, m) | 6.64) | ||||||||||||
| 1 a | 33.4 | 2.27 (Ha) (1H, d, J | – | C-2 a | 6 ʹ | 68.0 | 3.68 (1H, m) | H-7 ʹ | C-8, 5 ʹ | 8 ʹ | 170.8 | – | – | – |
| = 5.85) | ||||||||||||||
| 2.10 (Hb) (1H, d, J | ||||||||||||||
| = 5.66) | ||||||||||||||
| 2 a | 175.6 | – | – | – | 7 ʹ | 19.1 | 1.11 (3H, d, J = | – | 9 ʹ | 21.2 | 2.21 (3H, s) | – | C-8 ʹ | |
| 7.65) | ||||||||||||||
| 3 a | 64.2 | 4.17 (2H, t, J = | H-4 a | C-2 a | 1 a | 36.7 | 2.30 (Ha) (1H, d, | – | C-2 a | 1 a | 132.4 | – | – | – |
| 8.76) | J = 6.33) | |||||||||||||
| 2.08 (Hb) (1H, d, | ||||||||||||||
| J = 6.15) | ||||||||||||||
| 4a | 30.0 | 2.24 (2H, q, J = | H-5a | C-5a | 2a | 174.1 | – | – | – | 2a | 125.1 | 5.33 (1H, t, J = | H-3a | C-1a, |
| 6.92) | 8.65) | 3 a | ||||||||||||
| 5 a | 120.6 | 5.20 (1H, t, J = | – | C-3 a, 6 a | 3 a | 64.5 | 4.64 (2H, d, J = | H-4 a | C-2 a, 4 a | 3 a | 28.1 | 1.99 (2H, m) | – | C-4 a |
| 7.05) | 7.25) | |||||||||||||
| 6 a | 131.7 | – | – | – | 4 a | 129.5 | 5.37 (1H, q, J = | – | 5 a | 4 a | 27.4 | 2.01 (2H, m) | H-5 a | – |
| 6.75) | ||||||||||||||
| 7 a | 24.8 | 1.76 (3H, s) | – | 6a | 5a | 135.1 | 5.28 (1H, q, J = | H-6a | – | 5a | 123.5 | 5.23 (1H, t, J = | – | C-4a, |
| 7.05) | 6.82) | 6 a | ||||||||||||
| 8 a | 17.9 | 1.79 (3H, s) | – | 6 a | 6 a | 25.5 | 2.01 (2H, m) | H-7 a | 5 a | 6 a | 130.2 | – | – | – |
| 7 a | 14.3 | 1.02 (3H, d, J = | – | 6 a | 7 a | 24.6 | 1.84 (3H, s) | – | 6 a | |||||
| 8.65) | ||||||||||||||
| 8 a | 18.6 | 1.74 (3H, s) | – | 6a | ||||||||||
| 9a | 19.0 | 1.81 (3H, s) | – | 1a | ||||||||||