Table 1. Comparison of 1H and 13C NMR data for synthetic and natural phyllostictine A and ent-phaeosphaeride A in d6-DMSO.
Atom | Phyllostictine |
Atom |
ent-Phaeosphaeride A8a |
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Natural (Cox6) |
Synthetic (this work) |
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δC/ppm a | δH/ppm b , c | δC/ppm d | δH/ppm c , e | δC/ppm d | δH/ppm c , e | ||
1 | 166.4 | 166.5 | 1 | 166.5 | |||
3 | 137.1 | 137.1 | 3 | 137.1 | |||
4 | 155.3 | 155.3 | 4 | 155.3 | |||
5 | 104.8 | 104.8 | 5 | 104.8 | |||
6 | 64.4 | 3.86, d, J = 5.6 Hz | 64.3 | 3.79, s | 6 | 64.3 | 3.87, d, J = 5.5 Hz |
7 | 70.6 | 71.0 | 7 | 70.9 | |||
8 | 86.2 | 4.06, m | 86.3 | 4.00, d, J = 11.3 Hz | 8 | 86.2 | 4.07, d, J = 11.0 Hz |
9 | 27.5 | 1.82, m | 27.6 | 1.87–1.77, m | 9 | 27.6 | 1.82, m |
1.55, m | 1.56–1.49, m | 1.57–1.39, m | |||||
10 | 26.3 | 1.44, m | 26.5 | 1.46–1.40, m | 10 | 26.1 | 1.57–1.39, m, 2H |
1.33, m | 1.35–1.30, m | ||||||
11 | 31.1 | 1.26, m | 31.2 | 1.26, m | 11 | 30.9 | 1.36–1.10, m, 2H |
1.19, m | 1.19, m | ||||||
12 | 21.9 | 1.24, m | 22.1 | 1.24, m | 12 | 21.9 | 1.36–1.10, m, 2H |
13 | 28.5 | 1.25, m | 28.7 | 1.25, m | |||
14 | 28.4 | 1.25, m | 28.6 | 1.25, m | |||
15 | 13.8 | 0.85, t, J = 6.8 Hz, 3H | 14.0 | 0.79, t, J = 6.7 Hz, 3H | 13 | 13.8 | 0.86, t, J = 6.5 Hz, 3H |
16 | 90.5 | 4.95, d, J = 1.5 Hz | 90.9 | 4.96, s | 14 | 90.7 | 4.97, s, 2H |
4.96, d, J = 1.5 Hz | 4.96, s | ||||||
17 | 20.2 | 1.17, s, 3H | 19.9 | 1.11, s, 3H | 15 | 20.3 | 1.18, s, 3H |
18 | 63.6 | 3.78, s, 3H | 63.8 | 3.72, s, 3H | 16 | 63.7 | 3.79, s, 3H |
6-OH | 5.34, d, J = 5.9 Hz | 5.37, s | 6-OH | 5.42, d, J = 5.5 Hz | |||
7-OH | 4.84, s | 4.85, s | 7-OH | 4.90, s |
a100 MHz.
b400 MHz.
cIntegrate as 1H unless otherwise stated.
d125 MHz.
e500 MHz.