Table 1.
1H NMR Data (δ) for Compounds 1–5
| position | 1a | 2b | 3c | 4d | 5c |
|---|---|---|---|---|---|
| 3 | 4.96 br d (12.0) | 5.07 br d (12.0) | 4.91 br d (12.0) | 4.76 br d (11.4) | 5.33 br d (13.6, 3.2) |
| 5 | 3.53 dd (9.5, 6.0) | 3.61 t (8.0) | 3.50 dd (9.6, 6.4) | 3.49 dd (10.2, 6.6) | 4.14 t (9.6) |
| 6a | 4.02 dd (15.5, 9.5) | 4.00 dd (15.2, 8.0) | 4.17 dd (15.2, 9.6) | 3.85 dd (15.0, 8.4) | 3.75 dd (15.2, 11.2) |
| 6b | 3.20 dd (15.5, 6.0) | 3.37 dd (15.2, 8.0) | 3.25 dd (15.2, 6.4) | 3.25 dd (15.0, 6.6) | 3.58 dd (15.2, 7.2) |
| 9 | 7.70 d (7.5) | 7.69 d (8.0) | 7.77 d (7.2) | 7.53 dd (7.2, 1.2) | 7.77 d (8.0) |
| 10 | 7.14 dt (7.5, 2.0) | 7.13 td (8.0, 1.6) | 7.11 td (7.2, 1.6) | 7.07 dd (7.2, 1.2) | 7.10 t (8.0) |
| 11 | 7.08 td (7.5, 2.0) | 7.08 td (8.0, 1.6) | 7.09 td (7.2, 1.6) | 7.08 dd (7.2, 1.2) | 7.06 t (8.0) |
| 12 | 7.07 td (7.5, 2.0) | 7.06 t (8.0) | 7.15 dd (7.2, 1.6) | 7.10 dd (7.2, 1.2) | 7.13 d (8.0) |
| 14a | 3.08e | 2.96 m | 3.04 m | 3.08 br d (15.0) | 2.61 (dt, 16.0, 12.8) |
| 14b | 2.27 dt (15.0, 3.0) | 1.89 m | 2.34 m | 2.21 br d (15.0) | 1.94 ddd (16.0, 7.2, 3.2) |
| 15 | 2.98e | 2.97 t (7.2) | 2.82 dd (15.2, 11.2) | 2.89 | 3.81 dd (10.4, 7.2) |
| 17a | 3.89 d (8.5) | 3.82 (d, 8.8) | 3.74 d (8.8) | 3.85 d (8.4) | 3.59 br d (14.4) |
| 17b | 3.78 d (8.5) | 3.68 d (8.8) | 3.70 d (8.8) | 3.76 d (8.4) | 3.59 br d (14.4) |
| 18 | 1.43 d (5.5) | 1.34 d (4.8) | 1.40 d (5.6) | 1.45 d (5.4) | 1.62 d (7.2) |
| 19 | 3.05 q (5.5) | 3.04 q (4.8) | 3.03 q (5.6) | 3.09 q (5.4) | 5.10 q (7.2) |
| 21a | 3.57 s | 3.50 s | 3.63 s | 3.61 s | 4.26 br d (16.0) |
| 21b | 3.21 br d (16.0) | ||||
| 22a | 4.66 d (9.6) | ||||
| 22b | 4.57 d (9.6) | ||||
| NH | 9.88 s | 9.72 s | |||
| N-Me | 2.67 s | 2.73 s | 2.66 s | 2.70 s | |
| CO2Me | 2.34 s | 2.39 br s | 2.34 s | 2.27 s | 2.47 s |
| 3’a | 2.96e | 3.02e | 2.72e | 2.48 m | |
| 3’b | 2.72e | ||||
| 5’a | 3.13 ddd (14.5, 9.0, 6.5) | 3.12 m | 4.21 dd (12.0, 4.0) | 3.39 t (13.8) | 3.15 ddd (16.8, 13.6, 7.2) |
| 5’b | 3.07e | 3.12 m | 3.05 m | 2.89 | 3.15 ddd (16.8, 13.6, 7.2) |
| 6’a | 2.98e | 3.00 ddd (16.0, 9.6, 5.2) | 3.03e | 1.87 br d (12.0) | 2.95 dt (16.8, 6.4) |
| 6’b | 2.83 dt (16.5, 5.5) | 2.82 dt (16.0, 5.2) | 3.03e | 1.82 br d (12.0) | 2.83e |
| 9’ | 7.23 d (9.0) | 7.22 d (8.8) | 7.31 d (8.8) | 6.85 s | 7.23 d (8.0) |
| 10’ | 6.80 d (9.0) | 6.79 d (8.8) | 6.88 d (8.8) | 6.86 d (8.0) | |
| 11’ | |||||
| 12’ | 7.11 s | ||||
| 14’ | 1.23 m | 1.26 m | 1.85 m | 1.89 m | 1.53 br s |
| 15’a | 1.43 m | 1.30 m | 1.73 ddd (12.8, 9.6, 3.2) | 1.75 m | 1.46 m |
| 15’b | 1.02 m | 1.04 m | 1.06 ddt (12.8, 6.4, 2.4) | 1.07 m | 1.30 m |
| 17’a | 1.67 br d (14.0) | 1.79 br d (13.6) | 0.54 br d (13.6) | 2.73 br d (13.2) | 1.85 br d (13.6) |
| 17’b | 0.64 br d (14.0) | 0.74 br d (13.6) | 1.55 br d (13.6) | 2.39 br d (13.2) | 0.64 br d (13.6) |
| 18’ | 0.78 t (7.0) | 0.79 t (7.2) | 0.90 t (8.0) | 0.83 t (7.2) | 0.82 t (7.2) |
| 19’a | 1.30 m | 1.45 m | 1.43 m | 1.41 m | 1.27 m |
| 19’b | 1.01 m | 1.30 m | 1.26 m | 1.41 m | 1.12 m |
| 20’ | 1.03 m | 1.05 m | 1.60 m | 1.35 m | 1.11 m |
| 21’ | 3.33 br s | 3.33 br s | 4.33 br s | 3.73 s | 3.42 s |
| 22’a | 2.53 dd (16.5, 5.5) | 2.56 dd (16.0, 4.0) | 3.46 br d (10.4) | ||
| 22’b | 2.34 dd (16.5, 8.5) | 2.36 dd (16.0, 8.8) | 3.25 br d (10.4) | ||
| 24’ | 2.03 s | 2.03 s | |||
| CO2Me’ | 3.67 s | 3.71 s | 3.77 s | 3.64 s | 3.70 s |
| OMe-11’ | 3.92 s | 3.93 s | 3.96 s | 3.94 s | 3.96 s |
a
500 MHz, CDCl3.
b
800 MHz, CDCl3.
c
800 MHz, acetone-d6.
d
600 MHz, CDCl3.
e
Overlapped, without designating multiplicity.