Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution

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...

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Main Author: Ibrahim Ali , Noorbatcha
Format: Article
Language:English
Published: Wiley-VCH Verlag GmbH & Co. KGaA 2008
Subjects:
QD Chemistry
Online Access:http://irep.iium.edu.my/34905/
http://irep.iium.edu.my/34905/
http://irep.iium.edu.my/34905/
http://irep.iium.edu.my/34905/1/ChemEuroJ_2008.pdf
id iium-34905
recordtype eprints
spelling iium-349052014-02-12T01:33:16Z http://irep.iium.edu.my/34905/ Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution Ibrahim Ali , Noorbatcha QD Chemistry 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, CuBr(2), FeCl(3)6 H(2)O, FeCl(3)6 H(2)O/NaI, PbO(2), VOF(3)), 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 pi stacking. Wiley-VCH Verlag GmbH & Co. KGaA 2008-11-10 Article PeerReviewed application/pdf en http://irep.iium.edu.my/34905/1/ChemEuroJ_2008.pdf Ibrahim Ali , Noorbatcha (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 http://onlinelibrary.wiley.com/doi/10.1002/chem.200801575/abstract DOI: 10.1002/chem.200801575
repository_type Digital Repository
institution_category Local University
institution International Islamic University Malaysia
building IIUM Repository
collection Online Access
language English
topic QD Chemistry
spellingShingle QD Chemistry
Ibrahim Ali , Noorbatcha
Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: Influence of the solvent, oxidant, and substitution
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, CuBr(2), FeCl(3)6 H(2)O, FeCl(3)6 H(2)O/NaI, PbO(2), VOF(3)), 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 pi stacking.
format Article
author Ibrahim Ali , Noorbatcha
author_facet Ibrahim Ali , Noorbatcha
author_sort Ibrahim Ali , Noorbatcha
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
publisher Wiley-VCH Verlag GmbH & Co. KGaA
publishDate 2008
url http://irep.iium.edu.my/34905/
http://irep.iium.edu.my/34905/
http://irep.iium.edu.my/34905/
http://irep.iium.edu.my/34905/1/ChemEuroJ_2008.pdf
first_indexed 2023-09-18T20:50:11Z
last_indexed 2023-09-18T20:50:11Z
_version_ 1777409942020423680

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