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DOI: 10.1055/s-0040-1707257
Regioselective Biomimetic Synthesis of Dimeric Oxyresveratrol Derivatives
This research work was financially supported by the National Natural Science Foundation of China (No. 21462024).
Abstract
Oxyresveratrol and its methylated derivative as coupling precursors were efficiently prepared in four steps, with Wittig reactions and subsequent isomerization reactions as the key steps. The coupling reactions of oxyresveratrol under various oxidative conditions gave a complex and inseparable mixture of coupling products. The oxidative dimerizations of methylated oxyresveratrols catalyzed by horseradish peroxidase–H2O2 or FeCl3·6H2O in an acetone system predominantly produced the 8–5-coupled and 8–10-coupled dihydrobenzofuran-type dimers, respectively. This regioselective biomimetic strategy might be useful in synthesizing other dimeric oxyresveratrol derivatives.
Key words
oxyresveratrol - biomimetic synthesis - oligostilbenes - oxidative coupling - dimerization - regioselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707257.
- Supporting Information
Publication History
Received: 08 July 2020
Accepted: 03 August 2020
Article published online:
01 September 2020
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14
5-[(E)-2-(4-Hydroxy-2-methoxyphenyl)ethenyl]benzene-1,3-diol [(E)-15]
Pale-yellow oil; yield: 1.77 g (91%). 1H NMR (500 MHz, acetone-d
6): δ = 3.85 (s, 3 H), 6.24 (t, J = 2.0 Hz, 1 H), 6.46 (dd, J = 8.5, 2.0 Hz, 1 H), 6.49 (d, J = 2.0 Hz, 1 H), 6.52 (d, J = 2.0 Hz, 2 H), 6.88 (d, J = 16.5 Hz, 1 H), 7.30 (d, J = 16.5 Hz, 1 H), 7.45 (d, J = 8.5 Hz, 1 H), 8.16 (br s, 2 H), 8.51 (br s, 1 H). 13C NMR (125 MHz, acetone-d
6): δ = 55.8, 99.8, 99.9, 102.4, 105.5 (2 C), 108.5, 118.7, 123.9, 126.8, 127.9, 141.5, 159.2, 159.5, 159.6. HRMS (ESI): m/z [M –H]+ calcd for C15H13O4: 257.08193; found: 257.08191.
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15
5-{(E)-2-[3-(3,5-Dihydroxyphenyl)-2-(4-hydroxy-2-methoxyphenyl)-6-methoxy-2,3-dihydro-1-benzofuran-5-yl]ethenyl}benzene-1,3-diol (16)
Yellowish amorphous powder; yield: 31 mg (62%). 1H NMR (500 MHz, acetone-d
6): δ = 3.77 (s, 3 H), 3.94 (s, 3 H), 4.36 (d, J = 5.0 Hz, 1 H), 5.73 (d, J = 5.0 Hz, 1 H), 6.21 (d, J = 2.0 Hz, 2 H), 6.23 (t, J = 2.0 Hz, 1 H), 6.24 (t, J = 2.0 Hz, 1 H), 6.40 (dd, J = 8.5, 2.0 Hz, 1 H), 6.50 (d, J = 2.0 Hz, 2 H), 6.52 (d, J = 2.0 Hz, 1 H), 6.64 (d, J = 2.0 Hz, 1 H), 6.84 (d, J = 16.5 Hz, 1 H), 7.12 (d, J = 8.5 Hz, 1 H), 7.32 (d, J = 2.0 Hz, 1 H), 7.35 (d, J = 16.5 Hz, 1 H), 8.15 (br s, 2 H), 8.16 (br s, 2 H), 8.46 (br s, 1 H). 13C NMR (125 MHz, acetone-d
6): δ = 55.7, 56.2, 89.8, 94.3, 100.0, 102.0, 102.5, 105.5, 105.6 (2 C), 107.0, 107.1 (2 C), 107.6, 119.8, 121.2, 122.9 (2 C), 123.4, 123.9, 126.8, 128.1, 141.4, 147.2, 159.0, 159.1, 159.5, 159.6 (2 C), 162.2. HRMS (ESI): m/z [M – H]+ calcd for C30H25O8: 513.15549; found: 513.15547.
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16
5-{6-Hydroxy-2-(4-hydroxy-2-methoxyphenyl)-5-[(E)-2-(3-hydroxy-5-methoxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl}benzene-1,3-diol (18)
Yellowish amorphous powder; yield: 15 mg (45%). 1H NMR (500 MHz, acetone-d
6): δ = 3.76 (s, 3 H), 3.83 (s, 3 H), 4.36 (d, J = 5.0 Hz, 1 H), 5.67 (d, J = 5.0 Hz, 1 H), 6.20 (dd, J = 8.5, 2.0 Hz, 1 H), 6.26 (d, J = 2.0 Hz, 2 H), 6.34 (dd, J = 8.0, 2.0 Hz, 1 H), 6.36 (d, J = 2.0 Hz, 2 H), 6.41 (d, J = 2.0 Hz, 1 H), 6.51 (d, J = 2.0 Hz, 1 H), 6.68 (d, J = 2.0 Hz, 1 H), 6.76 (d, J = 16.5 Hz, 1 H), 7.05 (d, J = 8.0 Hz, 1 H), 7.15 (d, J = 16.5 Hz, 1 H), 7.16 (d, J = 8.0 Hz, 1 H). 13C NMR (125 MHz, acetone-d
6): δ = 55.6, 55.7, 55.8, 89.1, 99.7, 99.8, 103.9, 107.0, 107.3, 108.3, 118.6, 120.1, 122.3, 123.8, 125.3, 125.6, 127.2, 127.8, 128.1, 128.4, 137.2, 148.1, 151.9, 158.5 (2 C), 159.3 (2 C), 159.5, 162.8 (2 C). HRMS (ESI): m/z [M – H]+ calcd for C30H25O8: 513.15549; found: 513.15546.
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