JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
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3.2.1. Data for 2a (α:β = 1.27:1)
Yield = 73%, white solid. 1H NMR (500 MHz, CDCl3) δ: 6.87 (s, 0.45H, H-5), 6.77 (s, 0.56H,
H-5), 6.55 (s, 0.44H, H-8), 6.54 (s, 0.56H, H-8), 6.39 (s, 1.11H, 2′, 6′-H), 6.27 (s, 0.85H,
2′, 6′-H), 6.15 (d, J = 3.0 Hz, 0.44H, H-4), 6.00 (d, J = 4.5 Hz, 1.12H, OCH2O), 5.98 (d,
J = 3.0 Hz, 0.86H, OCH2O), 5.89 (d, J = 9.0 Hz, 0.56H, H-4), 4.67 (d, J = 5.0 Hz, 0.45H, H-1),
4.61 (d, J = 4.0 Hz, 0.58H, H-1), 4.34–4.40 (m, 1H, H-11), 4.22 (t, J = 10.0 Hz, 0.57H, H-11),
3.93 (t, J = 10.0 Hz, 0.53H, H-11), 3.81 (s, 1.73H, 4′-OCH3), 3.80 (s, 1.35H, 4′-OCH3), 3.76
(s, 3.41H, 3′, 5′-OCH3), 3.74 (s, 2.64H, 3′, 5′-OCH3), 3.25 (dd, J = 14.0, 5.0 Hz, 0.43H, H-2),
2.97–3.02 (m, 0.41H, H-3), 2.94 (dd, J = 14.5, 4.5 Hz, 0.60H, H-2), 2.81–2.87 (m, 0.58H,
H-3), 2.19 (s, 1.68H, CH3), 2.12 (s, 1.25H, CH3). 13C NMR (125 MHz, CDCl3) δ: 174.1, 173.6,
171.4, 170.5, 152.7, 152.6, 148.9, 148.1, 147.6, 147.4, 137.1, 134.8, 134.5, 132.9, 132.3, 128.3,
127.8, 110.2, 109.7, 109.5, 108.1, 107.0, 101.7, 101.6, 73.6, 71.3, 68.1, 67.4, 60.7, 56.2, 56.1,
45.6, 43.8, 43.7, 41.5, 38.7, 36.7, 21.1, 21.0. MS (ESI-TRAP) m/z (%): 479 ([M+Na]+, 100).
3.2.2. Data for 2b (α:β = 1.27:1)
Yield = 75%, white solid. 1H NMR (500 MHz, CDCl3) δ: 6.86 (s, 0.46H, H-5), 6.76 (s, 0.55H,
H-5), 6.55 (s, 0.44H, H-8), 6.54 (s, 0.56H, H-8), 6.39 (s, 1.11H, 2′, 6′-H), 6.28 (s, 0.90H,
2′, 6′-H), 6.16 (d, J = 3.0 Hz, 0.44H, H-4), 6.00 (d, J = 4.0 Hz, 1.15H, OCH2O), 5.98 (s,
0.89H, OCH2O), 5.90 (d, J = 9.0 Hz, 0.56H, H-4), 4.67 (d, J = 5.0 Hz, 0.46H, H-1), 4.61 (d,
J = 4.0 Hz, 0.56H, H-1), 4.34–4.39 (m, 1H, H-11), 4.23 (t, J = 10.0 Hz, 0.57H, H-11), 3.91 (t,
J = 10.0 Hz, 0.50H, H-11), 3.81 (s, 3H, 4′-OCH3), 3.76 (s, 3.45H, 3′, 5′-OCH3), 3.74 (s, 2.69H,
3′, 5′-OCH3), 3.25 (dd, J = 14.0, 5.0 Hz, 0.46H, H-2), 2.98–3.03 (m, 0.40H, H-3), 2.95 (dd,
J = 14.5, 4.5 Hz, 0.62H, H-2), 2.82–2.88 (m, 0.58H, H-3), 2.44–2.49 (m, 1.13H, CH2CH3),
2.36–2.42 (m, 0.88H, CH2CH3), 1.16–1.22 (m, 3H, CH2CH3). 13C NMR (125 MHz, CDCl3) δ:
174.8, 174.2, 174.0, 173.6, 152.7, 152.6, 148.8, 148.1, 147.6, 147.4, 137.3, 137.1, 134.8, 134.5,
132.8, 132.3, 128.4, 127.9, 110.2, 109.7, 109.5, 108.1, 108.0, 107.0, 101.7, 101.6, 73.4, 71.4,
67.8, 67.4, 60.7, 56.2, 56.1, 45.6, 43.8, 43.7, 41.5, 38.7, 36.8, 27.7, 27.6, 9.1. MS (ESI-TRAP)
m/z (%): 493 ([M+Na]+, 100).
3.2.3. Data for 2c (α:β = 1.27:1)
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Yield = 79%, white solid. H NMR (500 MHz, CDCl3) δ: 6.85 (s, 0.44H, H-5), 6.75 (s,
0.56H, H-5), 6.55 (s, 0.44H, H-8), 6.54 (s, 0.56H, H-8), 6.39 (s, 1.15H, 2′, 6′-H), 6.28 (s,
0.91H, 2′, 6′-H), 6.16 (d, J = 3.0 Hz, 0.46H, H-4), 5.99 (d, J = 2.0 Hz, 1.13H, OCH2O),
5.98 (d, J = 1.0 Hz, 0.87H, OCH2O), 5.90 (d, J = 9.0 Hz, 0.59H, H-4), 4.67 (d, J = 5.0 Hz,
0.45H, H-1), 4.61 (d, J = 4.0 Hz, 0.58H, H-1), 4.34–4.38 (m, 1H, H-11), 4.23 (t, J = 10.0 Hz,
0.57H, H-11), 3.91 (t, J = 10.0 Hz, 0.42H, H-11), 3.81 (s, 1.75H, 4′-OCH3), 3.80 (s, 1.37H,
4′-OCH3), 3.76 (s, 3.47H, 3′, 5′-OCH3), 3.74 (s, 2.71H, 3′, 5′-OCH3), 3.24 (dd, J = 14.0,
5.0 Hz, 0.45H, H-2), 2.97–3.00 (m, 0.46H, H-3), 2.95 (dd, J = 14.5, 4.5 Hz, 0.57H, H-2),
2.80–2.84 (m, 0.58H, H-3), 2.39–2.43 (m, 1.10H, CH2CH2CH3), 2.36 (t, J = 7.5 Hz, 0.96H,
CH2CH2CH3), 1.67–1.72 (m, 2H, CH2CH2CH3), 1.01 (t, J = 7.5 Hz, 1.71H, CH2CH2CH3),
0.97 (t, J = 7.5 Hz, 1.33H, CH2CH2CH3). 13C NMR (125 MHz, CDCl3) δ: 174.2, 174.0, 173.6,
173.2, 152.7, 152.6, 148.8, 148.1, 147.6, 147.4, 137.3, 137.1, 134.8, 134.5, 132.8, 132.3, 128.4,
127.9, 110.2, 109.7, 109.5, 108.1, 108.0, 107.0, 101.7, 101.6, 73.3, 71.4, 67.8, 67.4, 60.7, 56.2,
56.1, 45.5, 43.8, 43.7, 41.5, 38.8, 36.7, 36.3, 36.2, 18.5, 13.7. MS (ESI-TRAP) m/z (%): 507
([M+Na]+, 100).