ChemInform Abstract: STRUCTURAL RELATIONSHIP AND INTERCONVERSIONS OF ISOMERIC ASTILBINS

Isomerization of Dihydroquercetin

“…Consequently, inversion at C-3 of (+)rra«j-dihydroquercetin [1} by deprotonation and formation of an enediol (3) or inversion at both asymmetric carbons (23) would be expected to reduce the angle of rotation or lead to racemization, which is contrary to our results. The observed increase in the specific rotation on partial conversion of (+ )-transdihydroquercetin [1] to the less stable dr-isomer indicates a mechanism which involves heterocyclic ring opening to an intermediate quinone methide, as suggested previously (5).…”