Table 1.
1H NMR (500 MHz) and 13C NMR (125.7 MHz) data for 13–15 in CDCl3 (δ in ppm and J in Hz).
Carltonine A (13) | Carltonine B (14) | Carltonine C (15) | ||||
---|---|---|---|---|---|---|
Position | δ C | δ H | δ C | δ H | δ C | δ H |
1 | 59.2 | 2.58–2.46, m | 59.3 | 2.56–2.45, m | 55.2; 55.4 | 2.66–2.42, m |
2 | 32.8 | 2.65, t (7.4) | 32.7 | 2.66–2.58, m | 32.7; 32.8 | 2.66–2.42, m |
3 | 132.5 | 132.2 | 132.8 | |||
4 | 129.8 | 7.00–6.96, m | 129.7 | 7.00–6.94, m | 129.9 | 6.93–6.86, m |
5 | 115.1 | 6.72–6.68, m | 115.2 | 6.75–6.72, m | 114.9 | 6.71–6.65, m |
6 | 154.0 | 153.9 | 153.7 | |||
7 | 115.1 | 6.72–6.68, m | 115.2 | 6.75–6.72, m | 114.9 | 6.71–6.65, m |
8 | 129.8 | 7.00–6.96, m | 129.7 | 7.00–6.94, m | 129.9 | 6.93–6.86, m |
1′ | 58.5 | 3.45, d (14.0) 3.29, d, overlap (14.0) |
58.3 | 3.46, d (13.2) 3.27, d (13.2) |
55.1; 55.0 | 3.43, d (14.5) 3.29, d (14.5); 3.37, s |
2′ | 130.1 | 130.6 | 131.2; 131.0 | |||
3′ | 132.1 | 133.3 | 131.9; 131.8 | |||
4′ | 113.2 | 6.76, s | 110.2 | 6.75–6.72, m | 113.23; 113.15 | 6.74, s |
5′ | 146.9 | 145.9 | 146.7 | |||
6′ | 148.1 | 147.0 | 147.9 | |||
7′ | 111.1 | 7.10, s, overlap | 108.6 | 7.07, s, overlap | 110.6; 110.5 | 7.15, s; 7.14, s |
2″ | 57.1 | 3.32, dt, overlap (17.3, 8.8) 3.20, dt (17.3, 8.8) |
57.1 | 3.35, dt (17.5, 8.7) 3.16, dt (17.5, 8.7) |
57.1; 57.0 | 3.27–3.17, m |
3″ | 28.6 | 2.98, t (8.8) | 28.6 | 3.00–2.93, m | 28.6 | 2.99–2.91, m |
3a″ | 131.2 | 131.2 | 131.1 | |||
4″ | 123.3 | 7.09, dd, overlap (7.4, 1.0) | 123.4 | 7.08, d, overlap (7.4) | 123.3 | 7.07, d (7.4) |
5″ | 117.9 | 6.72, t, overlap (7.4) | 118.1 | 6.70, t, overlap (7.4) | 117.9; 117.8 | 6.71–6.65, m |
6″ | 130.5 | 6.82, dd (7.4, 1.0) | 130.4 | 6.79, d (7.4) | 130.3; 130.4 | 6.77, d (7.4) |
7″ | 123.0 | 122.9 | 122.8 | |||
7a″ | 150.4 | 150.4 | 150.3; 150.2 | |||
N-Me | 42.3 | 2.20, s | 41.9 | 2.18, s | - | - |
N1″-Me | 38.6 | 2.21, s | 38.8 | 2.23, s | 38.51; 38.48 | 2.14, s; 2.12, s |
5′-OMe | 55.8 or 55.9 | 3.34, s | - | - | 55.9 | 3.84, s |
6′-OMe | 55.8 or 55.9 | 3.34, s | - | - | 55.6 | 3.82, s; 3.81, s |
-OCH2O- | - | - | 101.0 | 5.99, s 5.98, s |
- | - |