A Unique Approach to the Concise Synthesis of Highly Optically Active Spirooxazolines and the Discovery of a More Potent Oxindole-Type Phytoalexin Analogue
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- 作者：Xianxing Jiang ; Yiming Cao ; Yiqing Wang ; Luping Liu ; Fangfang Shen ; Rui Wang
- 刊名：Journal of the American Chemical Society
- 出版年：2010
- 出版时间：November 3, 2010
- 年：2010
- 卷：132
- 期：43
- 页码：15328-15333
- 全文大小：388K
- 年卷期：v.132,no.43(November 3, 2010)
- ISSN：1520-5126
文摘
Drug-lead synthesis through rapid construction of chiral molecular complexity around the biologically relevant framework using a highly efficient strategy is a key goal of organic synthesis. Molecules bearing a spirooxindole-type framework exhibit important bioactivities. Herein, we present a highly efficient and convenient strategy that allows rapid construction of unique optically active spiro[oxazoline-3,3′-oxindole]s through the organocatalyzed asymmetric synthesis of spirocyclic thiocarbamates via an aldol reaction. Preliminary biological evaluation of several of the spirooxazolines using a model of acute neuroinflammation revealed promising antipyretic activity and provided an opportunity to discover new antipyretic agents.