通过[3,3] - 迁移重排对异米格拉他汀及其同系物进行热解：合成米格拉他汀及其类似物的新途径。
Thermolysis of isomigrastatin and its congeners via [3,3]-sigmatropic rearrangement: a new route to the synthesis of migrastatin and its analogues.
作者信息
Ju Jianhua, Lim Si-Kyu, Jiang Hui, Seo Jeong-Woo, Her Yeng, Shen Ben
机构信息
Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, University of Wisconsin-Madison, Madison, WI 53705, USA.
出版信息
Org Lett. 2006 Dec 7;8(25):5865-8. doi: 10.1021/ol062470p.
Abstract
Thermolysis of isomigrastatin (1) under neat heating conditions afforded migrastatin (1a). The reaction is proposed to proceed via a concerted [3,3]-sigmatropic rearrangement by which ring expansion is achieved regio- and enantiospecifically. The general applicability of this reaction was demonstrated with six additional isomigrastatin congeners (3-8), providing a new route to the synthesis of migrastatin analogues (3a-8a). [reaction: see text]
摘要
在纯加热条件下对异米格拉他汀（1）进行热解得到米格拉他汀（1a）。该反应被认为是通过协同的[3,3] - 西格玛重排进行的，通过这种重排可区域和对映体特异性地实现环扩展。用另外六种异米格拉他汀同系物（3 - 8）证明了该反应的普遍适用性，为米格拉他汀类似物（3a - 8a）的合成提供了一条新途径。[反应：见正文]
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