J. Wang et al. / Tetrahedron 71 (2015) 7687e7694
7691
6.91 (s, 1H), 6.79 (s, 1H), 5.39 (s, 2H), 3.90 (s, 3H), 3.89 (s, 3H), 3.71
(s, 2H). 13C NMR (100 MHz, CDCl3)
194.1, 173.1, 149.3, 147.1, 139.5,
33.4, 19.4, 19.1, 18.8, 18.7. HRMS (ESI): m/z [MþNa]þ calcd for
d
C38H32NaO4: 575.2191; found: 575.2193.
134.4, 132.0, 131.6, 129.3, 125.5, 120.6, 117.7, 113.5, 111.7, 107.8, 72.4,
56.0, 55.9, 25.7. HRMS (ESI): m/z [MþH]þ calcd for C19H17O4:
309.1120; found: 309.1121.
4.2.9. Compound 3b0. 99.7 mg (Yield 18%); yellow solid;
mp>300 ꢀC; IR (KBr): 3483, 2922, 1710, 1264, 770 cmꢁ1 1H NMR
(600 MHz, CDCl3)
8.09 (d, J¼7.2 Hz, 1H), 7.98 (d, J¼7.2 Hz, 1H),
.
d
4.2.4. Compound 1d. 354.5 mg (Yield 88%); yellow solid; mp
205.8e207.6 ꢀC; IR (KBr): 3450, 1708, 1627, 1592, 1399, 1140,
7.94e7.89 (m, 2H), 7.84 (d, J¼7.2 Hz, 1H), 7.59e7.52 (m, 2H), 7.46 (s,
1H), 7.13 (d, J¼7.8 Hz, 1H), 6.62 (d, J¼13.8 Hz, 2H), 6.53 (s, 1H),
4.55e4.48 (m, 2H), 4.07 (d, J¼6.6 Hz, 1H), 3.77 (br, 1H), 3.29e3.25
(m, 1H), 3.09e3.05 (m, 1H), 2.86e2.81 (m, 1H), 2.75e2.70 (m, 1H),
2.25 (s, 3H), 2.10 (s, 3H), 1.96 (s, 3H), 1.76 (s, 3H). 13C NMR (75 MHz,
717 cmꢁ1
;
1H NMR (600 MHz, CDCl3)
d
7.42 (d, J¼8.4 Hz, 1H), 7.38
(d, J¼6.6 Hz, 1H), 7.35 (d, J¼8.4 Hz, 1H), 7.29 (t, J¼7.2 Hz, 1H), 7.23 (t,
J¼7.2 Hz, 1H), 7.10 (d, J¼7.2 Hz, 1H), 5.72 (s, 2H), 4.06 (s, 2H). 13C
NMR (100 MHz, CDCl3)
d
193.1, 173.3, 143.4, 138.8, 134.9, 134.6,
CDCl3) d 203.6, 199.6, 199.5, 152.9, 143.3, 141.6, 136.8, 136.3, 136.2,
132.2, 132.2, 131.6, 124.5, 122.6, 121.0, 118.2, 106.2, 71.1, 26.0. HRMS
(ESI): m/z [MþNa]þ calcd for C17H10Br2NaO2: 426.8935; found:
426.8939.
136.1,135.8,135.3,134.9,134.5,134.3,133.4,133.1,132.6,131.5, 131.3,
130.3, 130.1, 129.4, 124.6, 124.0, 123.7, 123.6, 89.8, 68.8, 66.1, 56.5,
48.5, 34.4, 33.8,19.7, 19.5, 19.1, 18.9. HRMS (ESI): m/z [MþNa]þ calcd
for C38H32NaO4: 575.2189; found: 575.2193.
4.2.5. Compound 2a.15b 18.2 mg (Yield 8%); Yellow solid; mp
151.2e152.1 ꢀC; IR (KBr): 2963, 2926, 1708, 1632, 1602, 1262, 1102,
4.2.10. Compound 3c. 321.4 mg (Yield 52%); yellow solid; mp
176.5e179.7 ꢀC; IR (KBr): 3459, 2935, 1701, 1603, 1518, 1259,
1021 cmꢁ1 1H NMR (600 MHz, CDCl3)
. d 8.18 (s, 1H), 7.90 (d,
J¼7.8 Hz, 1H), 7.88 (s, 1H), 7.84 (d, J¼7.8 Hz, 1H), 7.76 (d, J¼7.8 Hz,
771 cmꢁ1
.
1H NMR (300 MHz, CDCl3)
d
7.97 (d, J¼7.8 Hz, 1H),
1H), 7.73 (d, J¼7.2 Hz, 1H), 7.55 (t, J¼7.8 Hz, 2H). 7.48 (t, J¼7.2 Hz,
7.79e7.74 (m, 2H), 7.67 (t, J¼7.5 Hz, 1H), 7.52 (d, J¼7.5 Hz, 1H),
7.45e7.35 (m, 2H), 7.02 (br, 1H), 6.96 (br, 1H), 6.94 (br, 1H), 6.45 (br,
1H), 6.32 (br, 1H), 6.25 (br, 1H), 5.52 (br, 1H), 5.40 (br, 1H), 4.45 (br,
1H), 3.92 (s, 3H), 3.78e3.74 (m, 4H), 3.68 (s, 3H), 3.60 (br, 3H), 2.87
1H), 7.36 (t, J¼7.2 Hz, 1H). 13C NMR (100 MHz, CDCl3)
d 193.1, 144.8,
138.3, 136.8, 136.1, 135.0, 133.5, 130.8, 129.1, 129.0, 128.7. 126.9,
125.6, 124.4, 120.9, 119.0, 109.7. HRMS (ESI): m/z [MþH]þ calcd for
C
17H11O: 231.0804; found: 231.0804.
(br,1H), 2.57 (br,1H). 13C NMR (75 MHz, CDCl3)
d 204.7, 202.4,198.9,
150.4,147.8, 147.5, 147.4,146.4,142.7, 142.2,137.3,136.6,136.0,135.0,
131.6, 130.9, 130.4, 130.0, 123.5, 123.4, 123.2, 122.9, 115.0, 114.7, 89.6,
65.1, 56.2, 55.7, 55.5, 55.4, 35.8, 33.6. HRMS (ESI): m/z [MþH]þ calcd
for C38H33O8: 617.2166; found: 617.2170.
4.2.6. Compound 3a. 308.8 mg (Yield 62%); pale yellow solid; mp
115.2e116.1 ꢀC; IR (KBr): 3468, 2897, 1697, 1594, 1257, 762 cmꢁ1. 1H
NMR (600 MHz, CDCl3)
d
7.96 (d, J¼7.8 Hz, 1H), 7.77 (d, J¼7.8 Hz,
1H), 7.72 (t, J¼7.2 Hz, 1H), 7.63 (t, J¼7.2 Hz, 1H), 7.54 (d, J¼7.8 Hz,
1H), 7.50 (d, J¼7.2 Hz, 1H), 7.41 (t, J¼7.8 Hz, 1H), 7.36 (t, J¼7.2 Hz,
1H), 7.19 (t, J¼7.8 Hz, 1H), 7.00 (t, J¼7.8 Hz, 1H), 6.92 (t, J¼8.4 Hz,
2H), 6.85 (d, J¼6.0 Hz, 1H), 6.81 (t, J¼6.6 Hz, 1H), 6.74 (d, J¼7.8 Hz,
1H), 6.70 (t, J¼7.2 Hz, 1H), 5.52 (br, 1H), 5.45 (br, 1H), 4.53 (br, 1H),
3.85 (br, 1H), 3.84 (br, 1H), 3.63 (br, 1H), 2.96 (br, 1H), 2.71 (br, 1H).
4.2.11. Compound 3c0. 160.7 mg (Yield 26%); yellow solid; mp
177.1e179.5 ꢀC; IR (KBr): 3446, 1709, 1632, 1517, 1266, 775 cmꢁ1. 1H
NMR (600 MHz, CDCl3)
d
8.06 (d, J¼6.6 Hz, 1H), 7.97 (d, J¼7.2 Hz,
1H), 7.91e7.87 (m, 2H), 7.80 (d, J¼7.2 Hz, 1H), 7.56e7.50 (m, 2H),
7.38 (s, 1H), 7.11 (d, J¼7.2 Hz, 1H), 6.67 (s, 1H), 6.38 (s, 1H), 6.32 (s,
1H), 4.50 (d, J¼9.6 Hz,1H), 4.46e4.43 (m,1H), 4.06 (d, J¼6.6 Hz,1H),
3.94 (s, 3H), 3.75 (s, 3H), 3.68 (s, 3H), 3.33 (s, 3H), 3.25e3.20 (m,
13C NMR (75 MHz, CDCl3)
d 203.9, 202.4, 199.0, 142.6, 142.0, 139.2,
138.7, 138.6, 137.3, 136.5, 135.8, 134.9, 132.7, 132.3, 131.3, 130.9,
129.9, 127.6, 126.1, 124.9, 123.5, 123.1, 89.8, 68.4, 66.9, 64.8, 44.2,
35.9, 33.8. HRMS (ESI): m/z [MþNa]þ calcd for C34H24NaO4:
519.1563; found: 519.1567.
1H), 3.08e3.03 (m, 1H), 2.80e2.76 (m, 1H), 2.71e2.66 (m, 1H). 13
C
NMR (100 MHz, CDCl3)
d 203.3, 199.4, 199.3, 152.7, 147.4, 146.9,
146.7, 146.2, 143.2, 141.4, 136.2, 136.0, 135.4, 131.7, 131.1, 130.3, 130.1,
127.2, 124.3, 124.1, 123.8, 123.6, 113.5, 113.4, 113.1, 112.5, 89.5, 67.9,
65.9, 57.6, 56.0, 55.9, 55.7, 55.6, 48.5, 33.9, 29.6. HRMS (ESI): m/z
[MþNa]þ calcd for C38H32NaO8: 639.1983; found: 639.1989.
4.2.7. Compound 3a0. 119.5 mg (Yield 24%); pale yellow solid; mp
134.0e136.1 ꢀC; IR (KBr): 3433, 1746, 1708, 1262, 762 cmꢁ1. 1H NMR
(600 MHz, CDCl3)
d
8.07 (d, J¼7.2 Hz, 1H), 7.96 (d, J¼7.2 Hz, 1H),
7.93e7.90 (m, 2H), 7.82 (d, J¼7.2 Hz, 1H), 7.70 (d, J¼7.8 Hz, 1H),
7.56e7.51 (m, 2H), 7.16 (t, J¼7.2 Hz, 1H), 7.11 (d, J¼7.3 Hz, 1H),
7.00e6.96 (m, 2H), 6.87e6.83 (m, 3H), 6.76 (t, J¼7.2 Hz, 1H),
4.60e4.55 (m, 2H), 4.10 (d, J¼6.0 Hz, 1H), 4.00 (br, 1H), 3.35e3.30
(m, 1H), 3.17e3.12 (m, 1H), 2.94e2.90 (m, 1H), 2.84e2.79 (m, 1H).
4.2.12. Compound 4d. 357.3 mg (Yield 88%); yellow solid; mp
130.1e133.2 ꢀC; IR (KBr): 2928, 1707, 1590, 1275, 760 cmꢁ1. 1H NMR
(600 MHz, CDCl3) d 7.99e7.98 (m, 1H), 7.93e7.92 (m, 1H), 7.87e7.83
(m, 2H), 7.19 (d, J¼8.4 Hz, 1H), 7.09 (d, J¼9.0 Hz, 1H), 4.26e4.24 (m,
1H), 3.62 (d, J¼3.6 Hz, 1H), 3.28 (dd, J¼15.0, 5.4 Hz, 1H), 3.16 (dd,
13C NMR (75 MHz, CDCl3)
d
203.4, 199.6, 199.4, 152.6, 143.2, 141.4,
J¼11.4, 3.0 Hz, 1H). 13C NMR (100 MHz, CDCl3)
d 198.5, 198.0, 145.7,
145.0, 142.7, 142.1, 135.9, 135.7, 132.5, 131.8, 123.4,123.3,115.0, 114.3,
139.4,138.9,137.5,136.3,136.2,136.0,135.4,135.1,130.4,130.1,129.7,
128.2, 127.9, 126.7, 126.7, 126.0, 125.9, 124.5, 124.1, 123.8, 123.8, 89.7,
68.2, 65.4, 56.8, 48.7, 34.4, 34.3. HRMS (ESI): m/z [MþNa]þ calcd for
52.8, 39.1, 32.9. HRMS (APCI): m/z [MþNa]þ calcd for
C17H10Br2NaO2: 426.8940; found: 426.8940.
C
34H24NaO4: 519.1565; found: 519.1567.
4.2.13. Compound 5a.20 203.4 mg (Yield 82%); yellow solid; mp
159.6e161.3 ꢀC; IR (KBr): 1681, 1582, 1378, 1346, 1210, 737 cmꢁ1. 1H
4.2.8. Compound 3b. 310.2 mg (Yield 56%); yellow solid; mp
288.3e290.5 ꢀC; IR (KBr): 3452, 1700, 1597, 1259, 771 cmꢁ1. 1H NMR
NMR (600 MHz, CDCl3)
J¼16.2 Hz, 2H), 7.82 (s, 2H), 7.42 (t, J¼7.2 Hz, 1H), 7.33 (t, J¼7.2 Hz,
1H), 7.28 (s, 1H), 2.55 (s, 3H). 13C NMR (100 MHz, CDCl3)
190.1,
d
8.54 (d, J¼7.8 Hz, 1H), 8.24 (s, 1H), 8.01 (d,
(600 MHz, CDCl3)
d
7.96 (d, J¼7.8 Hz, 1H), 7.76 (d, J¼7.8 Hz, 1H), 7.71
(t, J¼7.2 Hz, 1H), 7.61 (t, J¼7.2 Hz, 1H), 7.47 (d, J¼7.8 Hz, 1H), 7.39 (t,
J¼7.2 Hz, 1H), 7.35 (t, J¼7.2 Hz, 1H), 6.91 (d, J¼7.2 Hz, 1H), 6.67 (s,
1H), 6.57 (s, 1H), 6.47 (s, 1H), 5.59 (br, 1H), 5.35 (br, 1H), 4.44 (br,
1H), 3.83 (br, 1H), 3.73 (br, 1H), 3.54 (br, 1H), 2.88 (br, 1H), 2.59 (br,
1H), 2.19 (br, 3H), 2.07 (s, 3H), 1.89 (s, 3H), 1.82 (s, 3H). 13C NMR
d
188.6,144.1, 142.4,140.7, 139.9,135.3, 135.1,132.7, 132.4,131.3, 130.5,
129.0, 125.8, 123.2, 20.3. HRMS (ESI): m/z [MþH]þ calcd for
C17H13O2: 249.0909; found: 249.0910.
(100 MHz, CDCl3)
136.5, 136.3, 135.9, 135.8, 135.6, 135.5, 134.8, 134.6, 133.8, 133.6,
132.8, 129.9, 129.8, 123.5, 123.4, 123.0, 122.8, 89.7, 68.6, 64.9, 35.6,
d
204.1, 202.6, 198.9, 150.7, 142.7, 142.3, 137.4,
4.2.14. Compound 5b. 231.8 mg (Yield 84%); yellow solid; mp
184.0e185.9 ꢀC; IR (KBr): 1681, 1577, 1385, 1344, 1236, 743 cmꢁ1. 1H
NMR (600 MHz, CDCl3) d 8.55 (s, 1H), 8.23 (s, 1H), 8.00 (s, 2H), 7.81