Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution
Oligostilbenoids are polyphenols that are widely distributed in nature with multifaceted biological activities. To achieve biomimetic synthesis of unnatural derivatives, we subjected three resveratrol analogues to oligomerization by means of one-electron oxidants. Upon varying the metal oxidant (AgO...
| الحاوية / القاعدة: | Chemistry - A European Journal |
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| المؤلف الرئيسي: | |
| التنسيق: | مقال |
| اللغة: | English |
| منشور في: |
2008
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| الوصول للمادة أونلاين: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-57649171462&doi=10.1002%2fchem.200801575&partnerID=40&md5=d4958d7374bbb30f7940fc16a3ca820c |
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2-s2.0-57649171462 |
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2-s2.0-57649171462 Velu S.S.; Buniyamin I.; Ching L.K.; Feroz F.; Noorbatcha I.; Gee L.C.; Awang K.; Wahab I.Abd.; Weber J.-F.F. Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution 2008 Chemistry - A European Journal 14 36 10.1002/chem.200801575 https://www.scopus.com/inward/record.uri?eid=2-s2.0-57649171462&doi=10.1002%2fchem.200801575&partnerID=40&md5=d4958d7374bbb30f7940fc16a3ca820c Oligostilbenoids are polyphenols that are widely distributed in nature with multifaceted biological activities. To achieve biomimetic synthesis of unnatural derivatives, we subjected three resveratrol analogues to oligomerization by means of one-electron oxidants. Upon varying the metal oxidant (AgOAc, CuBr2, FeCl3·OH2O, FeCl3·O/H2O/NaI, PbO2, VOF3), the solvent (over the whole range of polarities), and the oxygenated substitution pattern of the starting material, stilbenoid oligomers with totally different carbon skeletons were obtained. Here we propose to explain the determinism of the type of skeleton produced with the aid of hard and soft acid/base concepts in conjunction with the solvating properties of the solvents and the preferred alignment by the effect of π stacking. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA. 15213765 English Article |
| author |
Velu S.S.; Buniyamin I.; Ching L.K.; Feroz F.; Noorbatcha I.; Gee L.C.; Awang K.; Wahab I.Abd.; Weber J.-F.F. |
| spellingShingle |
Velu S.S.; Buniyamin I.; Ching L.K.; Feroz F.; Noorbatcha I.; Gee L.C.; Awang K.; Wahab I.Abd.; Weber J.-F.F. Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution |
| author_facet |
Velu S.S.; Buniyamin I.; Ching L.K.; Feroz F.; Noorbatcha I.; Gee L.C.; Awang K.; Wahab I.Abd.; Weber J.-F.F. |
| author_sort |
Velu S.S.; Buniyamin I.; Ching L.K.; Feroz F.; Noorbatcha I.; Gee L.C.; Awang K.; Wahab I.Abd.; Weber J.-F.F. |
| title |
Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution |
| title_short |
Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution |
| title_full |
Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution |
| title_fullStr |
Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution |
| title_full_unstemmed |
Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution |
| title_sort |
Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution |
| publishDate |
2008 |
| container_title |
Chemistry - A European Journal |
| container_volume |
14 |
| container_issue |
36 |
| doi_str_mv |
10.1002/chem.200801575 |
| url |
https://www.scopus.com/inward/record.uri?eid=2-s2.0-57649171462&doi=10.1002%2fchem.200801575&partnerID=40&md5=d4958d7374bbb30f7940fc16a3ca820c |
| description |
Oligostilbenoids are polyphenols that are widely distributed in nature with multifaceted biological activities. To achieve biomimetic synthesis of unnatural derivatives, we subjected three resveratrol analogues to oligomerization by means of one-electron oxidants. Upon varying the metal oxidant (AgOAc, CuBr2, FeCl3·OH2O, FeCl3·O/H2O/NaI, PbO2, VOF3), the solvent (over the whole range of polarities), and the oxygenated substitution pattern of the starting material, stilbenoid oligomers with totally different carbon skeletons were obtained. Here we propose to explain the determinism of the type of skeleton produced with the aid of hard and soft acid/base concepts in conjunction with the solvating properties of the solvents and the preferred alignment by the effect of π stacking. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA. |
| publisher |
|
| issn |
15213765 |
| language |
English |
| format |
Article |
| accesstype |
|
| record_format |
scopus |
| collection |
Scopus |
| _version_ |
1792585536060260352 |