在合成萼花素I、萼花素J和表萼花素J共有的核心吡喃并色烯环系统中，π-堆积作为立体控制来源的证据。
Evidence for pi-stacking as a source of stereocontrol in the synthesis of the core pyranochromene ring system common to calyxin I, calyxin J, and epicalyxin J.
作者信息
Cakir Sidika Polat, Stokes Sean, Sygula Andrzej, Mead Keith T
机构信息
Department of Chemistry, Mississippi State University, Mississippi State, Mississippi 39762, USA.
出版信息
J Org Chem. 2009 Oct 2;74(19):7529-32. doi: 10.1021/jo901436u.
Abstract
A diastereoselective synthesis of the tetrahydropyranochromene ring system common to several natural product isolates of Alpinia blepharocalyx is reported. We have shown that a stereochemical preference exists for a syn configuration between the anomeric aryl substituents, representative of the C-7 and C-7' substituents in the natural products. Further, our results show that stereocontrol is under kinetic control, and calculations suggest that a favorable pi-stacking interaction may be the source of this stereocontrol.
摘要
报道了一种对山姜属植物艳山姜几种天然产物分离物中常见的四氢吡喃并色烯环系统的非对映选择性合成方法。我们已经表明，在天然产物中代表C-7和C-7'取代基的异头芳基取代基之间存在对顺式构型的立体化学偏好。此外，我们的结果表明立体控制是在动力学控制下进行的，计算表明有利的π-堆积相互作用可能是这种立体控制的来源。
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