手性全合成病毒素 A 和布比卡因。
Enantioselective total synthesis of virosaine A and bubbialidine.
机构信息
Department of Chemistry, University of Basel, St. Johanns-Ring 19, Basel 4056, Switzerland.
出版信息
Chem Commun (Camb). 2013 Mar 7;49(19):1921-3. doi: 10.1039/c3cc38783f. Epub 2013 Jan 30.
PMID:23364254
Abstract
The first enantioselective total syntheses of virosaine A and bubbialidine are described. Key transformations include the formation of a tetracyclic intermediate via an intramolecular aza-Michael addition, generation of a N-hydroxy-pyrrolidine through a Cope elimination and an intramolecular [1,3]-dipolar cycloaddition to generate a complex 7-oxa-1-azabicyclo[3.2.1]octane ring system.
摘要
首次对维罗沙胺 A 和布比他丁进行了对映选择性全合成。关键转化包括通过分子内氮杂迈克尔加成形成四环中间体，通过 Cope 消除和分子内 [1,3]-偶极环加成生成 N-羟基吡咯烷，从而生成复杂的 7-氧代-1-氮杂双环[3.2.1]辛烷环系统。
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