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

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

PDF ( Regio- and stereoselective biomimetic synthesis of oligostilbenoid dimers from resveratrol analogues: influence of the solvent, oxidant, and substitution) - Published Version Restricted to Registered users only Download (10MB) | Request a copy

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, 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.

Item Type:	Article (Journal)
Additional Information:	3704/34905
Uncontrolled Keywords:	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.
Subjects:	Q Science > QD Chemistry
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button):	Kulliyyah of Engineering > Department of Biotechnology Engineering
Depositing User:	Prof. Dr. Ibrahim Ali Noorbatcha
Date Deposited:	12 Feb 2014 09:33
Last Modified:	12 Feb 2014 09:33
URI:	http://irep.iium.edu.my/id/eprint/34905

Actions (login required)

View Item