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. 2022 Jun 13;23(12):6594. doi: 10.3390/ijms23126594

Table 2.

1H and 13C NMR spectral data of the new compounds 13 and 14 in CDCl3.

C/H 13 14
1 39.5 t 1.91 m
1.41 m
38.4 t 1.70 m
1.00 m
2 34.1 t 2.40 ddd (7.8, 4.6, 4.6)
2.50 ddd (7.8, 5.0, 5.1)
24.8 t 1.60 m
1.63 m
3 218.4 s - 81.0 d 4.48 dd
4 47.2 s - 37.6 s -
5 54.7 d 1.32 m 55.3 d 0.78 m
6 19.6 t 1.45 m
0.80 m
18.9 t 1.45 m
1.50 m
7 33.8 t 1.43 m
1.44 m
34.5 t 1.48 m
1.39 m
8 41.2 s - 41.4 s -
9 49.6 d 1.34 m 50.2 d 1.28 m
10 36.7 s - 37.8 s -
11 21.9 t 1.33 m
1.46 m
21.4 t 1.48 m
1.34 m
12 27.5 t 1.02 m
1.89 m
27.5 t 1.00 m
1.51 m
13 40.3 d 1.42 m 37.0 t 0.99 m
1.68 m
14 43.5 s - 43.5 s -
15 27.5 t 1.51 m
1.74 m
27.5 t 1.70 m
1.51 m
16 35.4 t 1.48 m
1.34 m
35.5 t 1.39 m
1.40 m
17 44.6 s - 44.7 s -
18 47.9 d 1.40 m 48.0 d 1.40 m
19 47.3 d 1.93 m 47.3 d 1.91 m
20 75.2 s - 75.2 s -
21 28.6 t 1.05 m
1.52 m
27.9 t 1.51 m
1.04 m
22 37.7 t 1.73 m
1.75 m
40.4 t 1.10 m
1.32 m
23 26.6 q 1.06 s 28.6 q 0.85 s
24 21.0 q 1.02 s 16.5 q 0.84 s
25 16.0 q 0.94 s 16.2 q 0.87 s
26 16.0 q 1.08 s 16.2 q 1.05 s
27 14.7 q 0.92 s 14.8 q 0.94 s
28 18.9 q 0.80 s 18.2 q 0.80 s
29 67.2 t 3.44 d (10.3)
3.65 d (10.3)
67.3 t 3.44 d (10.3)
3.63 d (10.3)
30 24.8 q 1.20 s 23.7 q 1.20 s
-COCH3 - - 171.0 s -
-COCH3 - - 21.3 q 2.03 s

The two protons at C-29 give their signals as doublets at ca. 3.40 and 3.60 ppm in both the compounds. The osmylation of 12 was completely stereoselective, giving rise to the new compound 14 as a single epimer. Similarly, compound 13 formed with a very high stereoselectivity (67% de, as established by 1H NMR) as an inseparable mixture of epimers. The absolute stereochemistry of the major epimers of both 13 and 14 has not been ascertained.