Synthesis of 3,3′-Di- O -methyl ardimerin and exploration of its DNA binding properties

Abstract

The 3,3′-di-O-methyl derivative (15) of the bis-C-aryl glycoside natural product ardimerin (1) has been synthesized in 11 steps from 2,3,4,6-tetrabenzylglucose (2) and 1,2,3-trimethoxybenzene (3). Key steps in the synthesis involve a Lewis acid mediated Friedel-Crafts type glycosylation and a Yamaguchi lactonization under Yonemitsu conditions. 3,3′-Di-O-methyl ardimerin aggregates in aqueous solutions at concentrations greater than 1 M, and both UV and fluorescence binding studies indicate that 15 has a low affinity for duplex DNA. © 2014 American Chemical Society.