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. Author manuscript; available in PMC: 2012 May 27.
Published in final edited form as: J Nat Prod. 2011 Mar 29;74(5):917–927. doi: 10.1021/np200076t

Table 1.

NMR Data for Veraguamide A (1) in CDCl3

unit C/H no δ Ca δH (J in Hz)b COSYb HMBCb
Br-Hmoya 1 170.8, C
2 42.4, CH 3.11, br q (7.4) H-3, H3-9 1, 3, 4, 9
3 76.4, CH 4.85, dt (10.2, 2.5) H-2, H-4a, H-4b 1, 1 (N-Me-Val-1)
4a 27.4, CH2 2.06, m H-3, H-4b, H-5a, H-5b 5, 6
4b 1.59, m H-3, H-4a, H-5a, H-5b
5a 25.0, CH2 1.60, m H-4a, H-4b, H-5b, H2-6 7, 8
5b 1.41, m H-4a, H-4b, H-5a, H2-6 6, 8
6 19.2, CH2 2.23, m H-5a, H-5b 7, 8
7 38.4, C
8 79.3, C
9 14.1, CH3 1.25, d (7.4) H-2 1, 2, 3
N-Me-Val-1 1 170.6, C
2 65.0, CH 3.93, d (10.3) H-3 1, 3, 4, N-Me, 1 (Pro)
3 28.3, CH 2.30, m H-2, H3-4, H3-5 2, 4, 5
4 19.56, CH3 0.98, d (6.6) H-3 2
5 19.51, CH3 0.91, d (6.6) H-3 2
N-Me 28.6, CH3 3.00, s 2, 1 (Pro)
Pro 1 172.1, C
2 57.3, CH 4.94 dd (8.9, 4.5) H-3a, H-3b 1, 3, 4, 1 (Hmpa)
3a 29.5, CH2 2.30, m H-2, H-3b, H-4a 1, 2, 5
3b 1.79, m H-2, H-3a, H-4a 1, 2, 5
4a 24.9, CH2 2.03, m H-3a, H-3b, H-4b, H-5a, H-5b 2, 3, 5
4b 1.98, m H-4a, H-5a, H-5b 2, 3, 5
5a 47.3, CH2 3.84, dt (−17.0, 7.1) H-4a, H-4b, H-5b 2, 3, 4
5b 3.61, dt (−17.0, 7.1) H-4a, H-4b, H-5a 3, 4
Hmpa 1 165.9, C
2 76.1, CH 4.90, d (9.1) H-3 1, 3, 4, 5, 1 (N-Me-Val-2)
3 35.7, CH 1.97, m H-2, H3-6
4a 24.81, CH2 1.54, m H-4b, H3-5
4b 1.13, m H-4a, H3-5
5 10.5, CH3 0.87, t (7.3) H-4a, H-4b 3, 4
6 13.8, CH3 1.01, d (6.8) H-3 2, 3, 4
N-Me-Val-2 1 169.6, C
2 66.0, CH 4.15, d (9.5) H-3 1, 3, 5, N-Me, 1(Val)
3 28.5, CH 2.27, m H-2, H3-4, H3-5 1
4 20.4, CH3 1.00, d (7.0) H-3 2
5 20.2, CH3 1.11, d (7.0) H-3 2, 3
N-Me 30.0, CH3 2.94, s 2, 1 (Val)
Val 1 173.4, C
2 52.8, CH 4.70, dd (8.7, 6.5) H-3, NH 1, 3, 4, 5, 1 (Br-Hmoya)
3 32.1, CH 1.96, m H-2, H3-4, H3-5 5
4 20.3, CH3 0.95, d (6.7) H-3 2, 3, 5
5 17.5, CH3 0.88, d (6.7) H-3 2, 3
NH 6.25, d (8.7) H-2 1, 1 (Br-Hmoya)
a

100 MHz

b

600 MHz