Table 1. 1H and 13C NMR Data of Truncatenolide (1)a and Its Esters (5 and 6)b.
1 |
5 | 6 | |||
---|---|---|---|---|---|
no. | δCc | δH (J in Hz) | HMBC | δH (J in Hz) | δH (J in Hz) |
2 | 172.7 s | H2C-3, H2C-4, H-10 | |||
3 | 37.3 t | 2.42 (1H) md | H2C-4 | 2.43 (1H) md | 2.45 (1H) md |
2.24 (1H) md | 2.25 (1H) md | 2.26 (1H) md | |||
4 | 30.2 t | 2.42 (1H) md | H-5, H-6, H2C-3 | 2.43 (1H) md | 2.45 (1H) md |
2.24 (1H) md | 2.25 (1H) md | 2.26 (1H) md | |||
5 | 130.9 d | 5.64 (1H) m | H2C-3, H2C-4 | 5.72 (1H) m | 5.84 (1H) m |
6 | 135.0 d | 5.31 (1H) dd (15.4, 8.8) | H2C-4, H2C-8 | 5.29 (1H) dd (15.4, 8.8) | 5.43 (1H) md |
7 | 74.9 d | 4.11 td (8.8, 6.6) | H2C-8, H2C-9, H-5 | 5.17 td (8.8, 6.6) | 5.43 (1H) md |
8 | 37.3 t | 1.96 (1H) m | H-10, H2C-9 | 1.95 (1H) m | 2.02 (1H) m |
1.61 (1H) md | 1.56 (1H) m | 1.58 (1H) m | |||
9 | 31.7 t | 1.76 (1H) dd (14.3, 7.7) | CH3 | 1.79 (1H) m | 1.90 (1H) m |
1.61 (1H) md | 1.61 (1H) m | 1.70 (1H) m | |||
10 | 72.8 d | 4.89 (1H) br quint (6.5) | H2C-8, H2C-9, CH3 | 4.89 (1H) br quint (6.5) | 4.95 (1H) br quint (6.5) |
CH3 | 22.2 q | 1.17 (3H) d (6.5) | H-9A | 1.18 (3H) d (6.5) | 1.20 (3H) d (6.5) |
OAc | 2.01 (3H) s | ||||
2′–6′ | 7.86 (2H) d (8.3) | ||||
3′–5′ | 7.56 (2H) d (8.3) |
2D 1H, 1H (COSY), and 13C, 1H (HSQC) NMR experiments confirmed the correlations of all of the protons and the corresponding carbons.
Coupling constants (J) are given in parentheses.
Multiplicities were assigned to the DEPT spectrum.
These two signals are in part overlapped.