Overcoming Synthetic Challenges of Oridonin A-Ring Structural Diversification: Regio- and Stereoselective Installation of Azides and 1,2,3-Triazoles at the C-1, C-2, or C-3 Position

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• 作者：Chunyong Ding ; Yusong Zhang ; Haijun Chen ; Christopher Wild ; Tianzhi Wang ; Mark A. White ; Qiang Shen ; Jia Zhou
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：July 19, 2013
• 年：2013
• 卷：15
• 期：14
• 页码：3718-3721
• 全文大小：282K
• 年卷期：v.15,no.14(July 19, 2013)
• ISSN：1523-7052

文摘

Efficient and concise synthetic approaches have been developed for the rapid and diverse installation of azide functionalities at the C-1, C-2, or C-3 positions of oridonin (1) with highly controlled regio- and stereoselectivity, while keeping key reactive pharmacophores intact by utilizing unique preactivation strategies based on the common synthon 4. Further functionalization of these azides through click chemistry yielding triazole derivatives successfully provides access to an expanded natural scaffold-based compound library for potential anticancer agents.