NMR data of compounds 1–3.
| 1a | 2a | 3b | ||||
|---|---|---|---|---|---|---|
| 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 | 30.5, CH2 | 1.13 (tdd, 13.5, 4.1, 1.4, 1H, α) | 29.2, CH2 | 1.24 (td, 13.5, 4.2, 1H, α) | 31.9, CH2 | 1.10 (td, 13.4, 4.2, 1H, α) |
| 2.79 (dtd, 13.8, 3.5, 1.5, 1H, β) | 3.23 (dddd, 13.9, 3.5, 3.3, 1.4, 1H, β) | 3.25 (dtd, 13.6, 3.3, 1.5, 1H, β) | ||||
| 2 | 18.2, CH2 | 1.58 (ddddd, 14.4, 4.4, 4.1, 3.3, 3.1, 1H, α) | 18.4, CH2 | 1.68 (dtt, 14.7, 4.1, 3.2, 1H, α) | 19.4, CH2 | 1.58 (ddddd, 14.4, 4.6, 4.2, 3.0, 2.8, 1H, α) |
| 1.68 (qt, 13.7, 3.5, 1H, β) | 1.78 (qt, 14.0, 3.6, 1H, β) | 1.99 (qt, 13.7, 3.9, 1H, β) | ||||
| 3 | 41.5, CH2 | 1.25 (td, 13.4, 4.4, 1H, α) | 41.2, CH2 | 1.32 (td, 13.5, 4.2, 1H, α) | 41.9, CH2 | 1.28 (td, 13.6, 4.6, 1H, α) |
| 1.53 (dtd, 13.4, 3.4, 1.5, 1H, β) | 1.54 (m, 1H, β) | 1.49 (dddd, 13.4, 4.1, 2.8, 1.5, 1H, β) | ||||
| 4 | 33.0, Cq | 33.4, Cq | 33.4, Cq | |||
| 5 | 52.7, CH | 1.31 (dd, 12.7, 2.0, 1H, α) | 53.6 | 1.51 (dd, 11.2, 4.0, 1H, α) | 53.5, CH | 1.41 (dd, 12.5, 2.8, 1H, α) |
| 6 | 17.8, CH2 | 1.75 (dddd, 13.6, 12.7, 10.7, 6.2, 1H, β) | 17.5, CH2 | 2.01 (m, 2H) | 17.7, CH2 | 1.95 (m, 1H, α) |
| 1.95 (ddt, 13.6, 7.2, 1.6, 1H, α) | 2.40 (m, 1H, β) | |||||
| 7 | 25.2, CH2 | 2.35 (dddt, 19.2, 10.7, 7.2, 1.1, 1H, α) | 24.9, CH2 | 2.43 (m, 1H, α) | 24.6, CH2 | 2.39 (m, 1H, α) |
| 2.48 (ddt, 19.2, 6.2, 1.2, 1H, β) | 2.58 (ddd, 19.3, 5.1, 2.2, 1H, β) | 2.53 (m, 1H, β) | ||||
| 8 | 161.6, Cq | 164.6, Cq | 163.6, Cq | |||
| 9 | 132.7, Cq | 126.8, Cq | 129.2, Cq | |||
| 10 | 40.7, Cq | 49.1, Cq | 44.3, Cq | |||
| 11 | 174.8, Cq | 171.2, Cq | 171.4, Cq | |||
| 12 | 71.4, CH2 | 4.65c (dd, 17.1, 1.1, 1H) | 71.1 | 4.68c (d, 18.3, 1H) | 71.0, CH2 | 4.64c (d, 17.3, 1H) |
| 4.71c (dt, 17,1, 1.0, 1H) | 4.72c (d, 18.3, 1H) | 4.66c (d, 17.3, 1H) | ||||
| 13 | 21.7, CH3 | 0.87 (s, 3H, β) | 21.6 | 0.80 (s, 3H, β) | 19.7, CH3 | 0.76 (s, 3H, β) |
| 14 | 33.3, CH3 | 0.96 (s, 3H, α) | 31.7 | 0.99 (s, 3H, α) | 32.3, CH3 | 0.96 (s, 3H, α) |
| 15 | 65.5, CH2 | 3.66 (dd, 10.8, 1.4, 1H, β) | 200.9 | 9.93 (s, 1H, β) | 173.9, Cq | |
| 4.14 (d, 10.8, 1H, β) | ||||||
| 16 | 52.1, CH3 | 3.68 (s, 3H, 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
Orientation could not be assigned with certainty.