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. Author manuscript; available in PMC: 2013 Jul 20.
Published in final edited form as: J Org Chem. 2012 Jul 3;77(14):6066–6075. doi: 10.1021/jo3008622

Table 1.

NMR data for Mandelalide A (1) in CDCl3

No. δC (mult) δH (J in Hz) COSY HMBC TOCSY ROESY
1 167.4 (s)
2 123.1 (d) 6.01 (dd, 15.5, 1.2) 3, 4a 1, 4 3, 4a, 4b, 5, 6ax, 6eq 3b, 4a, 4b, 5
3 147.1 (d) 6.97 (ddd, 15.2, 10.4, 4.6) 2, 4a, 4b 1, 2, 4, 5 2, 4a, 4b, 5, 6ax, 6eq 3b, 4ab, 4bb, 5
4a 38.8 (t) 2.36 (m) 2, 3 2, 3, 5, 6 2, 3, 5, 6ax, 6eq, 7 2, 3b, 5b, 6axb, 6eq
4b 2.39 (ddd, 14.1, 10.6, 10.6) 3, 5 2, 3, 5, 6 2, 3, 5, 6ax, 6eq, 7 2, 3b, 5b, 6axb, 6eq
5 73.9 (d) 3.36 (dddd, 11.4, 11.4, 2.3, 2.3) 4a, 4b, 6ax, 6eq 3, 4 2, 3, 4a, 4b, 6ax, 6eq, 7, 8ax, 8eq 2, 3, 4a, 4b, 6eq, 7
6ax 37.6 (t) 1.20 (m) 5, 6eq, 7 4, 5, 8 3, 4a, 4b, 5, 6eq, 7 4bb, 7
6eq 2.02 (dddd, 12.6, 4.4, 2.3, 1.6)a 5, 6ax, 7, 8eq 7, 8 4a, 4b, 5, 6ax, 7, 8ax, 6axb, 4a, 4b, 5, 7, 1′
7 73.1 (d) 3.82 (dddd, 11.1, 10.5, 4.4, 4.4)a 6ax, 6eq, 8ax, 8eq 8, 9, 1′ 4a, 4b, 5, 6ax, 6eq, 8ax, 8eq, 9 5, 6axb, 6eq, 8axb, 8eq, 9, 1′
8ax 39.7 (t) 1.22 (m) 7, 8eq, 9 6, 7, 9, 10 6eq, 7, 8eq, 9, 10b 6eqb, 7, 8eqb
8eq 1.87 (m) 6eq, 7, 8ax, 9 6, 7 6eq, 7, 8ax, 9, 10a, 10b 7, 8axb, 9, 10b, 5′
9 72.5 (d) 3.32 (dddd, 11.2, 11.2. 2.2, 2.2)a 8ax, 8eq, 10a, 10b 5, 7 6eq, 7, 8ax, 8eq, 10a, 10b, 11, 12, 13, 25 7, 8eq, 10a, 10bb, 25
10a 43.1 (t) 1.21 (ddd, 15.2, 9.6, 2.2)a 9, 10b, 11 11, 12, 25 8eq, 9, 10b, 12, 13, 14, 25 8eq, 9, 10bb, 11b, 12, 25
10b 1.51 (ddd, 15.2, 11.2, 3.7)a 9, 10a, 11 8, 9, 11, 12, 25 8ax, 8eq, 9, 10a, 11, 12, 13, 25 8eq, 9b, 10ab, 11, 25
11 34.2 (d) 2.37 (dqd, 9.6, 6.5, 3.7)a 10a, 10b, 12, 25 10, 12, 25 8ax, 8eq, 9, 10a, 10b, 11, 12, 13, 14, 15 10ab, 10b, 12b, 13, 25b
12 141.5 (d) 5.45 (dd, 14.8, 9.7) 11, 13 10, 11, 14, 25 9, 10a, 10b, 11, 13, 14, 15, 16a, 16b, 25 11b, 10a, 13b, 14b, 25
13 123.9 (d) 6.28 (dd, 14.8, 11.0) 12, 14 10, 11, 14, 15 10a, 10b, 11,12, 14, 15, 16a, 16b, 17, 25 11, 12b, 14b, 15b, 16b, 21
14 131.3 (d) 6.05 (dd, 10.9, 10.9) 13, 15 12, 13,16, 17 10a, 11, 12, 13, 15, 16a, 16b, 17, 25 12b, 13b, 15b, 16a
15 126.9 (d) 5.28 (ddd, 10.8, 10.8, 5.6) 14, 16a, 16b 13, 16, 17 12, 13, 14, 16a, 16b, 17, 18, 26 13b, 14b, 16a, 16bb, 17b
16a 31.1 (t) 1.88 (m) 14, 15, 16b, 17 14, 15, 17 12, 13, 14, 15, 16b, 17, 18, 19a, 26 14, 15, 16b, 17b, 26
16b 2.28 (ddd, 13.1, 11.4, 11.4) 15, 16a, 17 14, 15, 17, 18 12, 13, 14, 15, 16a, 17, 18, 19a, 19b, 26 13,15b,16a,17b,19a,21,26
17 81.0 (d) 3.98 (ddd, 11.1, 8.1, 1.8) 16a, 16b, 18 15, 19, 20 14, 15,16a, 16b, 18, 19a, 19b, 20, 21, 26 15, 16ab, 16bb,18, 26
18 37.3 (d) 2.52 (dddq, 12.0, 7.0, 7.0, 7.0)a 17, 19a, 19b, 26 16, 17, 19, 26 15, 16a, 16b,17, 19a, 19b, 20,21, 22a, 26 17, 19ab, 19b, 20, 26b
19a 36.8 (t) 1.17 (ddd, 11.9, 11.9, 10.3) 18, 19b, 20 18, 20, 21, 26 17, 18, 19a, 20, 21, 22a, 22b, 26 16b, 18b, 21, 22b, 26
19b 2.01 (ddd, 12.2, 7.0, 5.6)a 18, 19a, 20 17, 18 16b, 17, 18, 19a, 20, 21, 22a, 26 18, 19a, 20, 22a, 22b, 26
20 83.2 (d) 3.63 (m) 19a, 19b, 21 21, 22 17, 18, 19a, 19b, 21, 22a, 22b, 26 18, 19b, 21b, 22a, 22b
21 73.0 (d) 3.42 (ddd, 11.1, 8.8, 1.8) 20, 22a, 22b 20, 22, 23 17, 18, 19a, 19b, 20, 22a, 22b, 23, 24a, 24b, 26 13, 16b, 19a, 22ab, 22b, 23
22a 34.1 (t) 1.46 (ddd, 14.1, 11.1, 1.9) 21, 22b, 23 20, 21 18, 19a, 19b, 20, 21, 22b, 23, 24a, 24b, 26 19b, 21b, 22bb, 23, 24a, 24b
22b 1.76 (ddd, 13.9, 11.7, 1.8) 21, 22a, 23 23, 24 19a, 20, 21, 22a, 23,24a, 24b 19a, 19b, 21, 22ab,23b, 24a, 24b
23 72.3 (d) 5.23 (dddd, 11.7, 4.9, 2.9, 1.9) 22a, 22b, 24a, 24b 1 21, 22a, 22b, 24a, 24b 21, 22a, 22bb, 24a, 24b
24a 66.1 (t) 3.61 (m) 23, 24b 22, 23 23, 24b 22a, 22b, 23, 24b
24b 3.81 (dd, 12.2, 2.9)a 23, 24a 22, 23 22b, 23, 24a 22a, 22b, 23, 24a
25 18.3 (q) 0.85 (d, 6.6) 11 10, 11, 12 9, 10a, 10b, 11, 12, 13, 14 9, 10a, 10b, 11b, 12
26 14.5 (q) 1.03 (d, 6.9) 18 17, 18, 19 15, 16a, 16b, 17, 18, 19a, 19b, 20 21 16a, 16b, 18b, 19a, 19b
1′ 94.2 (d) 5.02 (d, 1.1) 2′ 7, 2′, 3′, 5′ 2′, 6′ 6eq, 7, 8eq, 2′, 7′
2′ 80.8 (d) 3.40 (dd, 3.8, 1.4) 1′, 3′ 3′, 4′, 7′ 1′, 3′, 4′, 5′, 6′, 8′, 9′ 1′
3′ 71.7 (d) 3.68 (m) 2′, 4′, 8′ 2′, 4′, 5′, 6′, 8′, 9′ 2′, 4′b
4′ 74.3 (d) 3.34 (dd, 9.4, 9.4) 3′, 5′ 3′, 5′, 6′ 3′, 5′, 6′, 8′, 9′ 3′b, 5′b, 6′
5′ 68.1 (d) 3.62 (m) 4′, 6′ 3′, 4′, 6′ 4′, 6′, 8′, 9′ 8eq, 4′b, 6′
6′ 17.7 (q) 1.27 (d, 6.3) 4′, 5′ 1′, 3′, 4′, 5′, 8′ 4′, 5′b
7′ 59.1 (q) 3.45 (s) 2′ 1′
OH-3′ 2.24 (s) 2, 4a, 4b 2′, 3′, 4′, 5′, OH-4′
OH-4′ 1.54 (s) 2, 3 3′, 4′, 5′, OH-3′

HMBC correlations are presented from proton to indicated carbon;

a

3JHH values obtained from DQFCOSY and/or NMRSim;

b

COSY artifacts observed in ROESY spectrum.