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. Author manuscript; available in PMC: 2021 Jul 2.
Published in final edited form as: J Org Chem. 2020 Jun 17;85(13):8462–8479. doi: 10.1021/acs.joc.0c00783

Table 1.

1H and 13C NMR (400/100 MHz, resp.) data of 1, 3, and 9 in CD3OD.

Unit Ring No 1a 3b 9b
1H (mult., J in Hz) 13C 1H (mult., J in Hz) 13C 1H (mult., J in Hz) 13C
I C 2 5.03, brs 77.1 100.1 100.3
3 3.89, dd (2.0, 1.0) 73.2 4.05, d, (3.4) 68.3 4.13, d, (3.5) 67.8
4 4.49, dd (2.0, 0.9) 37.0 4.45, d, (3.4) 29.5 4.20, d, (3.5) 29.5
A 5 157.6* 157.1 156.8
6 AB AB 6.03, d (2.4) 98.3 5.89, d (2.4) 98.0
7 157.8* 158.1 158.2
8 AB AB 6.08, d (2.4) 96.7 6.04, d (2.4) 96.5
9 158.1* 154.2 154.0
10 101.7 104.4 103.9
B 1′ 132.7 132.6 132.4
2′ 6.87, d (1.9) 115.0 7.16, d (2.1) 115.7 7.13, d (2.2) 115.7
3′ 145.8 145.6 145.6
4′ 145.5 146.7 146.8
5′ 6.71, d (8.2) 115.7 6.82, d (8.4) 115.6 6.80, d (8.4) 115.6
6′ 6.71, dd (8.2, 1.9) 119.1 7.03, dd (8.4, 2.1) 119.8 7.01, dd (8.4, 2.2) 119.9
II F 2 5.31, brs 79.1 4.54, d (9.8) 84.5
3 3.98, brd (1.9) 72.9 4.57, dd (9.8, 8.4) 73.0
4 4.56, brs 37.9 4.48, brd (8.4) 38.6
D 5 157.0 156.1
6 6.06, s 96.3 5.97, s 97.6
7 152.4 151.9
8 106.8 107.0
9 152.4 152.2
10 105.6 108.8
E 1′ 131.8 131.3
2′ 7.13, d (2.1) 116.2 7.07, d (2.1) 116.3
3′ 145.9 146.2
4′ 146.2 146.8
5′ 6.80, d (8.3) 116.1 6.84, d (8.2) 116.2
6′ 6.96, dd (8.3, 2.1) 120.6 6.95, dd (8.2, 2.1) 121.1
phloroglucinol 1″ 107.4 AB 107.5
2″&6″ 158.7 AB 159.7
3″&5″ 5.75, s 95.1 AB AB 5.79, s 95.5
4″ 160.0 AB 160.1
a,b

NMR data were acquired at a255 K, and b298 K

*

interchangeable assignment; AB: absence of signals.