Enantioselective Syntheses and Configuration Assignments of gamma-Chiral Butenolides from Plagiomnium undulatum:Butenolide Synthesis from Tetronic Acids

Tobias Kapferer; Reinhard Bruckner; Axel Herzig; Wilfried A.K6nigt

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Enantioselective Syntheses and Configuration Assignments of gamma-Chiral Butenolides from Plagiomnium undulatum:Butenolide Synthesis from Tetronic Acids

机译：宽叶疟原虫γ-手性丁烯内酯的对映选择性合成和构型分配：四丁酮酸合成丁烯内酯

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Both enantiomers of the gamma-chiral alpha,beta-dimethylated butyrolactones nat-1 and nat-2 from the moss Plagiomnium undulatum were synthesized stereoselec-tively through butenolides and tetronic acids,respectively.The configuration of the natural products was determined by GLC comparisons with mono(3-O-acetyl-6-O-tert-butyldimethylsilyl-2-O-methyl)hexakis(6-O-tert-butyldiniethylsilyl-2,3-di-O-methyl)-beta-cyclodextrin as a stationary phase.

机译：分别通过丁烯内酯和tetronic酸立体合成了苔藓天竺葵中γ-手性α，β-二甲基丁内酯nat-1和nat-2的两种对映异构体。单（3-O-乙酰基-6-O-叔丁基二甲基甲硅烷基-2-O-甲基）六（6-O-叔丁基二苯甲基乙基甲硅烷基-2,3-二-O-甲基）-β-环糊精为固定相。

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《Chemistry: A European journal》 |2005年第7期|共9页
作者
Tobias Kapferer; Reinhard Bruckner; Axel Herzig; Wilfried A.K6nigt;
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正文语种 eng
中图分类化学;
关键词
Arndt-Eistert homolo-gation; asymmetric synthesis; butyrolactones; configuration determination; dihydroxylation; tetronic acids;

机译：Arndt-Eistert同源性;不对称合成;丁内酯;构型确定;二羟基化;tetronic酸;

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1. Enantioselective Syntheses and Configuration Assignments of gamma-Chiral Butenolides from Plagiomnium undulatum:Butenolide Synthesis from Tetronic Acids [J] . Tobias Kapferer, Reinhard Bruckner, Axel Herzig, Chemistry: A European journal . 2005,第7期

机译：宽叶疟原虫γ-手性丁烯内酯的对映选择性合成和构型分配：四丁酮酸合成丁烯内酯
2. Enantioselective butenolide preparation for straightforward asymmetric syntheses of gamma-lactones - Paraconic acids, avenaciolide, and hydroxylated eleutherol [J] . Braukmuller S, Bruckner R European journal of organic chemistry . 2006,第9期

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3. Sharpless AD strategy toward the gamma-methyl butenolide unit of acetogenins: enantioselective synthesis of butenolide I and II with mosquito larvicidal activity [J] . He YT., Yang HN., Yao ZJ. Tetrahedron . 2002,第43期

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4. (Thio)Urea Derivatives in Enantioselective Hydrogen Bond Catalysis for γ- Butenolides Synthesis: A Joint Experimental-Theroretical Study(Abstracts) [C] . Margherita De Rosa, Luigi Cavallo, Lucia Citro European Symposium on Organic Chemistry . 2007

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5. Stereoselective Synthesis of Butenolides and its Applications in Total Synthesis of Sessilifoliamides and Development of New Chemical Tools for Hydrogel Based Biomaterials [D] . Li, Yi. 2017

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7. Fused and spiro furanones from tetronic acid synthons: Oxa and azacycles featuring the butenolide ring [O] . Urbina-Gonzalez Juan-Manuel 2006

机译：tetronic酸合成子的熔融和螺呋喃酮：具有丁烯内酯环的Oxa和氮杂环

Enantioselective Syntheses and Configuration Assignments of gamma-Chiral Butenolides from Plagiomnium undulatum:Butenolide Synthesis from Tetronic Acids

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