Velu, Saraswati S. and Buniyamin, Irmaizatussyehdany and Ching, Lee Kiew and Feroz, Fareeda and Noorbatcha, Ibrahim and Gee, Lim Chuan and Awang, Khalijah and Wahab, Ibtisam Abd and Weber, Jean-Frédéric Faizal (2008) Regio- and Stereoselective Biomimetic Synthesis of Oligostilbenoid Dimers from Resveratrol Analogues: Influence of the Solvent, Oxidant, and Substitution. Chemistry - A European Journal, 14 (36). pp. 11376-11384. ISSN 0947-6539, DOI https://doi.org/10.1002/chem.200801575.
Full text not available from this repository.Abstract
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.
| Item Type: | Article |
|---|---|
| Funders: | UNSPECIFIED |
| Uncontrolled Keywords: | Biomimetic synthesis; Hard/soft acids; Oxidation; Stacking interactions; Stilbene dimers |
| Subjects: | Q Science > Q Science (General) Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 01 Sep 2020 02:55 |
| Last Modified: | 01 Sep 2020 02:55 |
| URI: | http://eprints.um.edu.my/id/eprint/25482 |
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