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 (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.
Velu
Saraswati S
SS
Institut Kajian Ubat Semulajadi, Faculty of Pharmacy, Universiti Teknologi MARA, 40450 Shah Alam, Malaysia.
Buniyamin
Irmaizatussyehdany
I
Ching
Lee Kiew
LK
Feroz
Fareeda
F
Noorbatcha
Ibrahim
I
Gee
Lim Chuan
LC
Awang
Khalijah
K
Wahab
Ibtisam Abd
IA
Weber
Jean-Frédéric Faizal
JF
D032701:Biomimetics; D002384:Catalysis; D019281:Dimerization; D005419:Flavonoids / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry*; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry; D059808:Polyphenols; D000077185:Resveratrol; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry
D005419:Flavonoids; D016877:Oxidants; D010636:Phenols; D059808:Polyphenols; D012997:Solvents; D013267:Stilbenes; D000077185:Resveratrol