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. Author manuscript; available in PMC: 2018 Mar 24.
Published in final edited form as: J Nat Prod. 2017 Jan 18;80(3):726–730. doi: 10.1021/acs.jnatprod.6b00896

Table 2.

13C NMR Chemical Shifts of Ulapualides A-E (1–5) in CDCl3

position 1 2 3 4 5





δCa,b type δCa,b type δCa,b type δCa,c type δCa,c type
1 172.5 C 172.5 C 172.5 C 172.6 C 172.4 C
2 43.0 CH2 43.0 CH2 43.0 CH2 43.4 CH2 42.8 CH2
3 68.1 CH 68.1 CH 68.0 CH 69.0 CH 68.3 CH
4 37.1 CH2 37.1 CH2 37.1 CH2 37.5 CH2 37.0 CH2
5 20.8 CH2 20.7 CH2 20.8 CH2 29.8 CH2 20.5 CH2
6 43.8 CH2 43.7 CH2 43.8 CH2 36.8 CH2 43.7 CH2
7 210.5 C 210.4 C 210.5 C 71.2 CH 210.0 C
8 47.8 CH2 47.7 CH2 47.7 CH2 45.4 CH2 47.8 CH2
9 27.4 CH 27.3 CH 27.3 CH 31.1 CH 27.4 CH
9-Me 19.6 CH3 19.6 CH3 19.7 CH3 19.3 CH3 19.4 CH3
10 146.3 C 146.3 C 146.3 C 146.8 C 146.1 C
11 133.5 CH 133.5 CH 133.5 CH 133.8 CH 133.2 CH
12 154.1 C 154.1 C 154.1 C 154.4 C 153.8 C
13 130.1 C 130.0 C 129.8 C NDd NDd
14 137.3 CH 137.3 CH 137.3 CH 137.0 CH NDd
15 156.1 C 156.0 C 156.1 C 156.2 C 155.8 C
16 131.5 C 131.4 C 131.5 C NDd NDd
17 137.7 CH 137.7 CH 137.7 CH 137.3 CH NDd
18 162.7 C 162.7 C 162.7 C 162.9 C 162.4 C
19 116.9 CH 116.8 CH 116.8 CH 115.9 CH 116.9 CH
20 139.9 CH 140.0 CH 140.1 CH 141.4 CH 139.7 CH
21 33.8 CH2 33.9 CH2 34.0 CH2 35.0 CH2 33.4 CH2
22 79.9 CH 79.9 CH 79.9 CH 78.3 CH 79.6 CH
22-OMe 57.7 CH3 57.7 CH3 57.8 CH3 58.1 CH3 57.6 CH3
23 40.3 CH 40.3 CH 40.4 CH 41.0 CH 40.1 CH
23-Me 9.0 CH3 8.9 CH3 9.0 CH3 9.0 CH3 9.0 CH3
24 72.8 CH 72.9 CH 72.9 CH 72.6 CH 72.6 CH
25 31.9 CH2 31.8 CH2 32.1 CH2 33.6 CH2 31.6 CH2
26 81.7 CH 81.6 CH 81.1 CH 81.6 CH 81.4 CH
26-OMe 58.0 CH3 57.9 CH3 58.1 CH3 58.0 CH3 57.8 CH3
27 34.4 CH 34.7 CH 35.5 CH 34.5 CH 34.4 CH
27-Me 15.4 CH3 15.5 CH3 15.4 CH3 15.7 CH3 15.6 CH3
28 25.0 CH2 27.0 CH2 28.4 CH2 25.2 CH2 26.6 CH2
29 39.8 CH2 30.4 CH2 29.7 CH2 39.8 CH2 30.3 CH2
30 211.6 C 73.03 CH 70.0 CH 211.6 C 72.7 CH
31 48.6 CH 37.5 CH 39.7 CH 48.6 CH 37.2 CH
31-Me 13.3 CH3 9.7 CH3 8.5 CH3 13.6 CH3 9.1 CH3
32 77.2 CH 79.8 CH 79.3 CH 77.2 CH 76.4 CH
32-OAc 170.0 C 170.6 C 172.5 C 170.0 C 171.1 C
20.8 CH3 20.9 CH3 20.9 CH3 20.9 CH3 20.8 CH3
33 36.8 CH 36.9 CH 36.5 CH 36.9 CH 36.7 CH
33-Me 18.8 CH3 19.3 CH3 19.4 CH3 19.0 CH3 19.4 CH3
34 110.4 CH 110.2 CH 110.0 CH 110.5 CH 109.5 CH
35 129.4 CH 129.4 CH 129.4 CH 129.4 CH 129.4 CH
35-NMe 27.5 CH3 27.5 CH3 27.5 CH3 27.5 CH3 27.5 CH3
35-NCHO 162.1 CH 162.1 CH 162.1 CH 162.1 CH 161.9 CH
36 170.2 C 170.3 C
37 80.6 CH 81.4 CH
37-OMe 58.6 CH3 58.2 CH3
38 72.98 CH2 62.9 CH2
38-OMe 59.3 CH3
a

Carbon spectra recorded at 125 MHz.

b

Resonances for minor rotamers can be found in the supporting information.

c

Carbon resonances extrapolated from HSQC and HMBC experiments.

d

Not detected.