Synthesis of 3,3′-Di‑O‑methyl Ardimerin and Exploration of Its DNA Binding Properties

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 Yamagu...

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Bibliographic Details
Published in:Organic letters 2014-04, Vol.16 (8), p.2212-2215
Main Authors: Mavlan, Miran, Ng, Kevin, Panesar, Harmanpreet, Yepremyan, Akop, Minehan, Thomas G
Format: Article
Language:English
Subjects:
Anisoles - chemistry
DNA - metabolism
Fluorescence
Glycosylation
Lactones - chemical synthesis
Lactones - chemistry
Letter
Molecular Structure
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Summary: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 μM, and both UV and fluorescence binding studies indicate that 15 has a low affinity for duplex DNA.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500725e