NMR data of compounds 4–6.
| 4b,c | 5a | 6b | ||||
|---|---|---|---|---|---|---|
| δ C | δ H (mult., J in Hz) | δ C | δ H (mult., J in Hz) | δ C | δ H (mult., J in Hz) | |
| 1 | 68.5, CH | 3.82 (m, 1H, β) | 31.9, CH2 | 1.11 (td, 13.4, 4.2, 1H, α) | 32.6, CH2 | 1.32 (tdd, 13.6, 3.8, 0.7, 1H, α) |
| 3.25 (dtd, 13.6, 3.4, 1.4, 1H, β) | 2.62 (dt, 13.6, 3.6, 1H, β) | |||||
| 2 | 26.6, CH2 | 1.65 (dq, 14.9, 3.3, 1H, α) | 19.3, CH2 | 1.59 (ddddd, 14.5, 4.4, 4.2, 3.1, 2.8, 1H, α) | 27.3, CH2 | 1.68 (tdd, 13.4, 11.7, 3.8, 1H, β) |
| 1.94 (dddd, 14.9, 14.3, 4.0, 2.5, 1H, β) | 2.00 (qt, 14.0, 3.9, 1H, β) | 1.79 (ddt, 13.4, 4.6, 3.6, 1H, α) | ||||
| 3 | 34.8, CH2 | 1.25 (ddd, 13.7, 4.0, 3.0, 1H, β) | 41.9, CH2 | 1.28 (td, 13.5, 4.4, 1H, α) | 78.6, CH | 3.29 (dd, 11.7, 4.6, 1H, α) |
| 1.74 (td, 14.0, 3.9, 1H, α) | 1.51 (dddd, 13.4, 4.0, 2.8, 1.5, 1H, β) | |||||
| 4 | 33.1, Cq | 33.6, Cq | 38.8, Cq | |||
| 5 | 38.0, CH | 2.18 (dd, 11.1, 6.9, 1H, α) | 53.3, CH | 1.43 (dd, 12.4, 2.6, 1H, α) | 51.5, CH | 1.17 (dd, 12.4, 1.8, 1H, α) |
| 6 | 23.6, CH2 | 2.03 (m, 1H, β) | 17.7, CH2 | 1.96 (m, 1H, α) | 18.0, CH2 | 1.62 (dddd, 13.6, 12.4, 11.3, 6.0, 1H, β) |
| 2.33 (m, 1H, α) | 2.42 (m, 1H, β) | 1.94 (ddt, 13.6, 7.0, 1.6, 1H, α) | ||||
| 7 | 120.5, CH | 5.75 (m, 1H) | 24.5, CH2 | 2.42d (m, 1H) | 25.4, CH2 | 2.30 (dddt, 19.0, 11.3, 7.0, 1.3, 1H, α) |
| 2.53d (m, 1H) | 2.43 (ddt, 19.0, 6.0, 1.2, 1H, β) | |||||
| 8 | 133.6, Cq | 164.3, Cq | 159.1, Cq | |||
| 9 | 49.0, CH | 3.36 (m, 1H, α) | 128.7, Cq | 135.2, Cq | ||
| 10 | 48.6, Cq | 44.2, Cq | 34.6, Cq | |||
| 11 | 105.5, CH | 5.68 (d, 4.4, 1H) | 171.3, Cq | 172.2, Cq | ||
| 12 | 72.3, CH2 | 4.39 (m, 2H) | 71.0, CH2 | 4.65d (d, 17.3, 1H) | 70.6, CH2 | 4.57d (dt, 16.9, 1.0, 1H) |
| 4.69d (d, 17.3, 1H) | 4.60d (dd, 16.9, 1.2, 1H) | |||||
| 13 | 20.2, CH3 | 0.73 (s, 3H, β) | 19.9, CH3 | 0.86 (s, 3H, β) | 15.4, CH3 | 0.87 (s, 3H, β) |
| 14 | 30.9, CH3 | 0.95 (s, 3H, α) | 32.3, CH3 | 0.97 (s, 3H, α) | 28.2, CH3 | 1.07 (s, 3H, α) |
| 15 | 69.6, CH2 | 3.58 (d, 8.6, 1H, α) | 178.2, Cq | 20.0, CH3 | 1.16 (d, 0.7, 3H, β) | |
| 3.82 (d, 8.6, 1H, β) | ||||||
a
Recorded at 500 MHz (1H) or 125 MHz (13C), CDCl3, 298 K, δH and δC in ppm.
b
Recorded at 700 MHz (1H) or 175 MHz (13C), CDCl3, 298 K, δH and δC in ppm.
c
Also recorded at 700 MHz (1H) or 175 MHz (13C) in CD3OD (298 K) to prevent signal overlapping of H-15 and H-1 in the 1H NMR spectrum that was crucial for the elucidation of the stereochemistry (for NMR data see ESI Table S6).
d
Orientation could not be assigned with certainty.