Dynamic NMR investigation of two new interconvertible diasteriomeric epimers of natural 2-benzyl-2-hydroxybenzofuranone derivative from Pterocarpus marsupium

The first example of a pair of interconvertible diastereomeric epimers 2α/2β-hydroxy-2-p-hydroxybenzyl-3(2H)-benzofuranone-7-C-β-d-glucopyranoside isolated from the heartwood of Pterocarpus marsupium is reported. The predominance of over was supported by dynamic exchange rates and activation parameters obtained from NMR studies. The mechanism of this unique phenomenon is thought to be operative by the formation of diketone as suggested by deuterium exchange.