A Unique Approach to the Concise Synthesis of Highly Optically Active Spirooxazolines and the Discovery of a More Potent Oxindole-Type Phytoalexin Analogue

被引：284

作者：

Jiang, Xianxing ^{[1
,2
]}

Cao, Yiming ^{[1
]}

Wang, Yiqing ^{[1
]}

Liu, Luping ^{[1
]}

Shen, Fangfang ^{[1
]}

Wang, Rui ^{[1
,2
]}

机构：

[1] Lanzhou Univ, Key Lab Preclin Study New Drugs Gansu Prov, Inst Biochem & Mol Biol, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Hong Kong Polytech Univ, Key Lab Chirosci, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 43期

关键词：

CATALYTIC ENANTIOSELECTIVE SYNTHESIS; DOUBLY STEREOCONTROLLED APPROACH; ASYMMETRIC MICHAEL ADDITION; ALPHA-ISOTHIOCYANATO IMIDES; CONJUGATE ADDITION; ALDOL REACTION; NITROALKENES; AMINE; CONSTRUCTION; STEREOCENTERS;

D O I：

10.1021/ja106349m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：15328 / 15333

页数：6

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