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. Author manuscript; available in PMC: 2018 Feb 3.
Published in final edited form as: J Org Chem. 2017 Jan 18;82(3):1316–1329. doi: 10.1021/acs.joc.6b02161

Table 3.

1H (900 MHz) and 13C (225 MHz) NMR Spectroscopic Data of Compounds 5 and 6a,b

unit/ring no. 5
6
unit/ring no. 5
6
δC, mult δH (J, Hz) δC, mult δH (J, Hz) δC, mult δH (J, Hz) δC, mult δH (J, Hz)
unit I unit III
C 2 99.98, C 100.00, C I 2 84.53, CH 4.6620, ddd (8.2, 0.1,–0.5) 100.38, C
3 68.59, CH 4.0246, d (3.1) 68.48, CH 3.9870, d (3.0) 3 68.46, CH 4.0860, ddd (8.7, 8.2, 5.7) 67.73, CH 4.0867, d (3.4)
4 29.82, CH 4.6816, d (3.1) 29.78, CH 4.6718, d (3.0) 4 29.58, CH2 3.0091, dd (−16.5, 5.7)
2.5730, ddd (−16.5, 8.7,0.5)
29.63, CH 4.3001, d (3.4)
A 5 157.84, C 157.90, C G 5 156.13, C 150.70, C
6 97.74, CH 6.0059, d (2.4) 97.74, CH 6.0327, d (2.3) 6 96.28, CH 6.0862, s 110.18, C
7 158.11, C 158.15, C 7 152.70, C 152.96, C
8 96.33, CH 6.0483, d (2.4) 96.34, CH 6.0610, d (2.3) 8 107.33, C 97.27, CH 6.2523, s
9 154.33, C 154.35, C 9 151.12, C 152.73, C
10 103.67, C 103.55, C 10 103.28, C 106.36, C
B 1′ 132.67, C 132.62, C H 1′ 130.79, C 132.09, C
2′ 115.42, CH 7.0972, dd (2.2, 0.2) 115.21, CH 7.0325, dd (2.2, 0.2) 2′ 116.03, CH 6.9638, ddd (2.1, −0.5, <0.1c) *115.59, CH 7.1191, dd (2.2, < 0.1c)
3′ 145.61, C 145.56, C 3′ 146.76, C 145.72, C
4′ 146.27, C 146.65, C 4′ 146.70, C 146.92, C
5′ 115.64, CH 6.7815, dd (8.3, 0.2) *115.61, CH 6.7469, dd (8.4, 0.2) 5′ 116.26, CH 6.8303, dd (8.2, < 0.1c) *115.60, CH 6.8077, dd (8.3, <0.1c)
6′ 119.65, CH 6.9929, dd (8.3, 2.2) 119.76, CH 6.9858, dd (8.4, 2.2) 6′ 120.73, CH 6.8829, dd (8.2, 2.1) 119.83, CH 7.0109, dd (8.3, 2.2)
unit II unit IV
F 2 100.76, C 100.95, C L 2 85.00, CH 4.6119, ddd (9.1, −0.2, 0.1)
3 67.82, CH 4.0997, d (3.2) 67.57, CH 4.1187, d (3.1) 3 68.01, CH 4.2543, ddd (9.1,9.1,6.1)
4 29.65, CH 4.3194, d (3.2) 30.15, CH 4.3878, d (3.1) 4 30.61, CH2 3.1288 dd (−16.4, 6.1)
2.5768, ddd (−16.4, 9.1,0.1)
D 5 155.85, C 155.51, C J 5 156.31, C
6 98.12, CH 6.1168, s 98.11, CH 6.1955, s 6 96.61, CH 6.0824, s
7 153.45, C 153.56, C 7 152.26, C
8 108.80, C 109.12, C 8 106.38, C
9 148.97, C 148.89, C 9 151.69, C
10 105.42, C 105.19, C 10 103.71, C
E 1′ 132.41, C 132.31, C K 1′ 130.22, C
2′ 115.50, CH 7.4033, dd (2.2, 0.2) 115.53, CH 7.4221, dd (2.2, < 0.1c) 2′ 117.27, CH 7.0656, ddd (2.0, −0.2, 0.2)
3′ 145.61, C 145.62, C 3′ 146.23, C
4′ 146.89, C 146.86, C 4′ 147.06, C
5′ 115.68, CH 6.8809, dd (8.3, 0.2) 115.70, CH 6.8914, dd (8.3, < 0.1c) 5′ 116.69, CH 6.9201, dd (8.2, 0.2)
6′ 120.30, CH 7.4232, dd (8.3, 2.2) 120.34, CH 7.4374, dd (8.3, 2.2) 6′ 121.04, CH 7.0707, dd (8.2, 2.0)
a

1H and 13C NMR data were acquired in methanol-d6 at 298 K at 900 and 225 MHz, respectively.

b

The δH and J values including their signs were generated via 1H iterative full spin analysis (HiFSA).11

c

Very small couplings were detected by HiFSA (for pms profiles, see the Supporting Information) and are essential for the line overall fit. Asterisks indicate that the signals are interchangeable.