吲哚-2-甲酸和(S)-吲哚啉-2-甲酸的合成和相互转化研究进展有机化学.pdfVIP

2011 年第 31 卷 有 机 化 学 Vol. 31, 2011 第 5 期, 634～645 Chinese Journal of Organic Chemistry No. 5, 634～645 ·综述与进展· 吲哚-2- 甲酸和(S)-吲哚啉-2- 甲酸的合成和相互转化研究进展 刘金强 a,b 钱 超 a 陈新志*,a (a 浙江大学化学工程与生物工程学系 杭州 310027) (b 洛阳师范学院化学化工学院 洛阳 471022) 摘要 吲哚-2- 甲酸和(S)-吲哚啉-2- 甲酸均是具有生物活性的天然产物和众多降压药的特征结构片段, 报道了它们的合 成及其相互转化研究进展. 吲哚啉-2- 甲酸可由吲哚-2- 甲酸还原制得, 其中(S)-吲哚啉-2- 甲酸可由外消旋体拆分或通过 不对称合成法制备, 其中“手性源法”作为一种新出现的方法具有较好的前景. 吲哚-2- 甲酸可由 Fischer 吲哚合成法制 备, 或通过取代苯胺或苯甲醛制备, 也可通过吲哚啉衍生物氧化脱氢制备, 其中 Fischer 合成法仍具有较强的竞争力. 关键词 吲哚-2- 甲酸; 吲哚啉-2- 甲酸; 相互转化; 研究进展 Syntheses of Indole-2-carboxylic Acid and Indoline-2-carboxylic Acid and Transformation from Each Other Liu, Jinqianga,b Qian, Chaoa Chen, Xinzhi*,a a ( Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027) (b College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022) Abstract Indole-2-carboxylic acid and indoline-2-carboxylic acid are common building block in natural products with bioactivities and anti-hypertension pharmaceuticals. The syntheses and transformation from each other were reviewed. Indoline-2-carboxylic acid can be got from the reduction of indole-2-carboxylic acid and the S enantiomer can be achieved from the resolution of the racemic mixture with chemical reagents or enzymes. The chiral pool synthesis, emerged recently, will play an important role