Synthesis of 3,3鈥?Di-O-methyl Ardimerin and Exploration of Its DNA Binding Properties

详细信息    查看全文

• 作者：Miran Mavlan ; Kevin Ng ; Harmanpreet Panesar ; Akop Yepremyan ; Thomas G. Minehan
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：April 18, 2014
• 年：2014
• 卷：16
• 期：8
• 页码：2212-2215
• 全文大小：286K
• 年卷期：v.16,no.8(April 18, 2014)
• ISSN：1523-7052

文摘

The 3,3鈥?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鈥揅rafts type glycosylation and a Yamaguchi lactonization under Yonemitsu conditions. 3,3鈥?Di-O-methyl ardimerin aggregates in aqueous solutions at concentrations greater than 1 渭M, and both UV and fluorescence binding studies indicate that 15 has a low affinity for duplex DNA.