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. Author manuscript; available in PMC: 2019 Apr 27.
Published in final edited form as: J Org Chem. 2018 Oct 26;83(22):13670–13677. doi: 10.1021/acs.joc.8b01609

Table 1.

1H and13C NMR data for lepadin I (1) (TFA salt, CDCl3, 23˚ C)

1Ha, δ, mult (J, Hz) 13Cb δ (mult) COSYa NOESYa HMBCa
1
2 3.49, m 55.8 (CH) 9, 3 3, 4ax 9
3 5.04, q (2.8) 67.8 (CH) 2, 4ax, 4eq 2,4ax, 4eq, 9 1”, 4, 5, 9
4ax 2.48, d (15.6) 28.9 (CH2) 3, 4eq, 5 3, 4eq, 4a, 1’ 2, 3, 8a, 4a, 5
4eq 1.63, mc 3, 4ax 3, 4ax, 4a, 8a, 4a, 5
4a 1.54, md 37.5 (CH) 4eq, 5 4ax, 4eq, 8a, 5, 6ax 3, 8a, 5,
5 1.95, m 34.5 (CH) 4a, 6ax, 4a, 1’, 2’, 6ax 4a, 6, 1’,
6ax 0.81, qd (12.6, 3.3) 31.2 (CH2) 5, 6eq, 7eq, 7ax 4a, 5, 6eq, 7ax, 7eq, 8ax 4a, 5, 7,8
6eq 1.87, brd (12.6) 6ax, 7ax, 7eq 5, 6ax, 1’, 2’ 4a, 8,
7eq 1.54, md 19.9 (CH2) 6eq, 7ax, 6ax, 8eq, 7ax 8a, 5
7ax 1.74, qt (13.5, 3.3) 6eq, 6ax, 7eq, 8eq, 8ax 6ax, 8eq, 7eq, 6, 8
8αx 1.64, mc 29.3 (CH2) 8a, 8eq, 7ax 6ax, 8a, 8eq, 8a, 4a, 6, 7
8eq 2.01, d (14.5) 8a, 8ax, 7eq 7ax, 7eq, 8ax 8a, 4a, 6, 7
8a 3.46, m 57.4 (CH) 4a, 8ax, 8eq 4ax, 4a, 8ax, 8eq 7
9 1.31, mh 14.8 (CH3) 2 3, 2” 2, 3
1” 164.6 (Cq)
2” 5.74, d (14.9) 111.7 (CH) 4” 4” 2, 1”, 3”
3” 8.07, d (14.9) 150.0 (CH) 3” 3” 1”, 2”, 5”
4”
5” 2.33, s, 3H 14.2 (CH3) 3”
1’ 0.92, mf
1.36, me
33.1 (CH2) 2’ 4eq, 5, 6eq 5, 3’, 2’
2’ 1.07, m
1.31, me
26.1 (CH2) 1’, 3’ 5, 6eq 1’, 3’
3’ 1.20, mg 30.3 (CH2) 2’, 4’ 1’, 4’, 5’
4’ 1.24, mg 30.0 (CH2) 3’ 6’, 5’ 3’,
5’ 1.26, mg
1.36, me
25.8 (CH2) 7’,
6’ 1.39, me 37.7 (CH2) 7’
7’ 3.57, m 71.8 (CH) 6’, 8’ 5’, 9’
8’ 1.39, me 39.9 (CH2) 7’, 9’
9’ 1.35, me
1.44, me
19.3 (CH2) 8’, 10’ 7’, 8’
10’ 0.91, t (6.8)f 14.3 (CH3) 9’ 8’, 9’
NH 8.23, bs
a

600 MHz, in the presence of Et2NH•TFA buffer (~20 mM).

b

, 150 MHz, multiplicities assigned by APT and edited HSQC.

c-h

overlapped signals. i signal overlapped.