Thermolysis of isomigrastatin and its congeners via [3,3]-sigmatropic rearrangement: a new route to the synthesis of migrastatin and its analogues |
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| Authors: | Ju Jianhua Lim Si-Kyu Jiang Hui Seo Jeong-Woo Her Yeng Shen Ben |
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| Institution: | Division of Pharmaceutical Sciences, University of Wisconsin National Cooperative Drug Discovery Group, University of Wisconsin-Madison, Madison, WI 53705, USA. |
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| 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] |
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