Table 1.
NMR spectral data forpseurotins in CDCl3.
| Position | Pseurotin A1 (1) | Pseurotin A2 | 3 | 5 | ||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| δH a | m, J/Hz | δC | δH a | m, J/Hz | δC | δH a | m, J/Hz | δC | δH a | m, J/Hz | δC | |||||
| 1 | ||||||||||||||||
| 2 | 183.4 | qC | 183.5 | qC | 186.0 | qC | 186.4, | qC | ||||||||
| 3 | 113.2 | qC | 114.3 | qC | 113.4 | qC | 114.8, | qC | ||||||||
| 4 | 196.2 | qC | 199.7 | qC | 196.5 | qC | 201.1, | qC | ||||||||
| 5 | 89.5 | qC | 87.3 | qC | 92.7 | qC | 86.5, | qC | ||||||||
| 6 | 169.4 | qC | 166.9 | qC | 166.8 | qC | 167.5, | qC | ||||||||
| 7 | 8.53 | s | 7.70 | s | 8.38 | s | 7.34 | s | ||||||||
| 8 | 96.5 | qC | 93.2 | qC | 90.5 | qC | 96.4, | qC | ||||||||
| 9 | 4.88 | s | 76.6 | CH | 4.42 | br d, 12.0 (9-OH) | 74.2 | CH | 4.69 | br s | 73.2 | CH | 4.86 | d, 5.4 (9-OH) | 78.6, | CH |
| 10 | 4.60 | br s | 70.5 | CH | 4.73 | d, 3.0 (11) | 70.1 | CH | 4.59 | d, 5.4 (11) | 70.7 | CH | 4.69 | br d, 5.4 (11) | 70.9, | CH |
| 11 | 4.76 | d, 7.8 (12) | 71.0 | CH | 4.94 | dd, 8.4 (12) 3.0 (10) |
70.6 | CH | 4.75 | dd, 10.8 (12) 5.4 (10) |
70.7 | CH | 4.81 | dd, 10.8 (12) 5.4 (10) |
69.6, | CH |
| 12 | 5.23 | dd, 10.8 (13) 7.8 (11) |
126.4 | CH | 5.28 | dd, 10.8 (13) 8.4 (11) |
125.3 | CH | 5.28 | dd, 11.2 (13) 10.8 (11) |
126.4 | CH | 5.43 | dd, 11.2 (13) 10.8 (11) |
125.6, | CH |
| 13 | 5.64 | dt, 10.8 (12) 7.2 (14) |
136.9 | CH | 5.64 | dt, 10.8 (12) 7.2 (14) |
137.4 | CH | 5.59 | dt, 11.2 (12) 7.8 (14) |
136.8 | CH | 5.74 | dt, 11.2 (12) 7.8 (14) |
138.2, | CH |
| 14A | 2.09 | m | 21.4 | CH2 | 2.14 | m | 21.4 | CH2 | 2.09 | m | 21.4 | CH2 | 2.15 | m | 21.5, | CH2 |
| 14B | 2.15 | m | 2.19 | m | 2.15 | m | 2.21 | m | ||||||||
| 15 | 0.99 | t, 7.8 (14) | 14.1 | CH3 | 1.03 | t, 7.2 (14) | 14.1 | CH3 | 0.98 | t, 9.0 (14) | 14.1 | CH3 | 1.05 | t, 7.2 (14) | 14.2, | CH3 |
| 16 | 1.68 | s | 6.2 | CH3 | 1.67 | s | 5.9 | CH3 | 1.68 | s | 6.0 | CH3 | 1.78 | s | 5.6, | CH3 |
| 17 | 194.3 | qC | 194.0 | qC | 195.2 | qC | 192.4, | qC | ||||||||
| 18 | 133.5 | qC | 132.8 | qC | 132.4 | qC | 133.8, | qC | ||||||||
| 19 | 8.27 | d, 8.4 (20) | 130.0 | CH | 8.34 | d, 8.4 (20) | 130.7 | CH | 8.31 | d, 8.4 (20) | 130.7 | CH | 8.20 | d, 8.4 (20) | 129.4, | CH |
| 20 | 7.49 | t, 8.4 (19, 21) | 128.8 | CH | 7.48 | t, 8.4 (19, 21) | 128.6 | CH | 7.49 | t, 8.4 (19, 21) | 128.7 | CH | 7.50 | t, 8.4 (19, 21) | 128.8, | CH |
| 21 | 7.64 | t, 8.4 (20, 22) | 134.4 | CH | 7.63 | t, 8.4 (20, 22) | 134.6 | CH | 7.64 | t, 8.4 (20, 22) | 134.7 | CH | 7.63 | t, 8.4 (20, 22) | 134.2, | CH |
| 22 | 7.49 | t, 8.4 (21, 23) | 128.8 | CH | 7.48 | t, 8.4 (21, 23) | 128.6 | CH | 7.49 | t, 8.4 (21, 23) | 128.7 | CH | 7.50 | t, 8.4 (21, 23) | 128.8, | CH |
| 23 | 8.27 | d, 8.4 (22) | 130.0 | CH | 8.34 | d, 8.4 (22) | 130.7 | CH | 8.31 | d, 8.4 (22) | 130.7 | CH | 8.20 | d, 8.4 (22) | 129.4, | CH |
| 8-OCH3 | 3.37 | s | 51.7 | CH3 | 3.30 | s | 51.9 | CH3 | 3.44 | s | 51.8 | CH3 | 3.27 | s | 51.5, | CH3 |
| 9-OH | 3.94 | br s | 4.22 | br d, 12.0 (9) | 4.25 | br s | 4.97 | d, 5.4 (9) | ||||||||
a 1H chemical shift values (δ ppm from SiMe4) followed by multiplicity and then the coupling constants (J/Hz). Figures in parentheses indicate the proton coupling with that position.