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. Author manuscript; available in PMC: 2017 Feb 15.
Published in final edited form as: Eur J Med Chem. 2015 Dec 24;109:36–46. doi: 10.1016/j.ejmech.2015.12.041

Table 1.

NMR data for derivatives 4, 13, and 24 (1H NMR: 300 MHz; 13C NMR: 75 MHz).

Position 4 (CDCl3) 13 (CDCl3) 24 (CDCl3)
δC, type δH, J in Hz) δC, type δH, (J in Hz) δC, type δH, (J in Hz)
2 83.2, CH 5.00, d (12.0) 145.3, C - 155.6, C -
3 72.6 (72.5), CH 4.55 (4.54), d (12.0) 136.2, C - 138.6, C -
4 195.9, C - 175.4, C - 179.1, C -
4a 100.8, C - 104.0, C - 106.1, C -
5 163.8, C - 160.9, C - 162.1, C -
6 96.1, CH 6.12 (6.11), d (2.1) 98.6, CH 6.36, s 98.5, CH 6.33, d (2.1)
7 168.7, C - 165.6, C - 165.2, C -
8 95.2, CH 6.05 (6.04), d (2.1) 92.7, CH 6.45, s 92.6, CH 6.40, d (2.1)
8a 163.0, C - 157.0, C 156.9, C -
10 78.5, CH 4.03–4.08, m 78.9, CH 4.16-4.12, m 78.9, CH 4.15-4.10, m
11 76.6 (76.5), CH 4.97, d (8.4) 76.6, CH 5.01, d (8.4) 76.5, CH 5.01, d (8.4)
12a 144.12 (144.09), C - 144.0, C - 143.7, C -
13 117.5 (117.2), CH 7.08 (7.11), d (1.8) 116.9, CH 7.88, s 117.8, CH 7.77, d (2.1)
14 129.72 (129.67), C - 124.5, C - 124.3, C -
15 121.3 (121.05), CH 7.11 (7.08), dd (8.1, 1.8) 121.9, CH 7.83, d (8.4) 122.9, CH 7.74, dd (8.4, 2.1)
16 116.8 (116.6), CH 7.21, dd (7.2, 1.5) 117.4, CH 7.10, d (8.4) 117.1, CH 7.06, d (9.0)
16a 144.32 (144.27), C - 145.1 C - 145.7 C -
17 128.0, C - 127.8, C - 127.8, C -
18 109.7, CH 6.94, t (1.5) 109.7, CH 6.98, s 109.7, CH 6.98, s
19 147.1, C - 147.2, C - 147.1, C -
20 146.6, C - 146.7, C - 146.7, C -
21 114.8, CH 6.96, s 114.9, CH 6.99, s 114.9, CH 7.00, s
22 121.0, CH 6.96, s 121.1, CH 6.99, s 121.0, CH 7.00,
23 61.9, CH2 3.82, dd (12.6, 2.7) 61.9, CH2 3.86, dd (12.6, 3.6) 61.8, CH2 3.86, dd (12.6, 2.1)
3.57, dd (12.6, 4.2) 3.60, dd (12.6, 3.6) 3.60, dd (12.6, 3.0)
graphic file with name nihms748884t1.jpg 70.4, CH2 3.96-3.92, overlapped 68.6, CH2 4.03, t (6.6) 68.9, CH2 4.01, t (6.6)
22.4, CH2 1.80, Hex (7.5) 31.1, CH2 1.81 quin (7.5) 31.9 CH2 1.85-1.69 m
- - 19.3, CH2 1.51 Hex (7.5) 30.2,a 29.1, 26.1, 22.8 (CH2)n 1.48-1.28 m
10.5, CH3 1.02, t (7.5) 14.0 CH3 1.00, t (7.5) 14.2 CH3 0.90 t(6.6)
graphic file with name nihms748884t2.jpg - - - - 73.1, CH2 4.01, t (6.6)
- - - - 31.9 CH2 1.85-1.69 m
- - - - 29.2,a 29.1, 26.1, 22.8. (CH2)n 1.48-1.28 m
- - - - 14.2 CH3 0.88 t(6.9)
19-OMe 56.2, CH3 3.93, s 56.3, CH3 3.95, s 56.2, CH3 3.94, s
3-OH - - - 6.54, s - -
5-OH - 11.18 (11.17), s - 11.67, s - 12.65, s
20-OH - 5.75, s - 5.79, s - 5.75, s
23-OH - - - - - 2.05, s
a

These two signals are exchangeable.