Diastereoselective Entry to Novel Aminoindolizidines with Fused Furan, Thiophene, and Pyrrole Ring Starting from L‐Glutamic Acid

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2025-02-10 DOI:10.1002/ejoc.202401219
Paula Fraňová , Peter Šafář , Ján Moncoľ , Ivana Žídeková , Prof. Adam Daïch , Štefan Marchalín
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Abstract

A series of novel optically pure aminoindolizidines featuring fused tetrahydro‐furan, thiophene, or pyrrole ring were synthesized from the proteinogenic L‐glutamic acid as a chiral precursor and a nitrogen atom source. The synthetic sequence employed tricyclic indolizidinols as advanced building blocks, which were prepared on a gram‐scale from bioavailable reagents. Key transformations within the used synthetic sequence included diastereoselective Thompson azidation, Staudinger reduction, Jurjew reaction, and highly diastereoselective catalytic hydrogenation. These steps facilitated the efficient and stereoselective synthesis of the ultimate amino‐ and N‐acetylamino‐indolizidines.

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以l -谷氨酸为起始原料,用呋喃、噻吩和吡咯环进行非对映选择性合成新型氨基吲哚吡啶
以蛋白质源l -谷氨酸为手性前体和氮原子源,合成了一系列具有四氢呋喃、噻吩或吡咯环融合的新型光学纯氨基吲哚嘧啶。该合成序列以三环吲哚吡啶醇为高级构件,由生物可利用试剂以克为单位制备。合成序列中的关键转化包括非对映选择性汤普森叠氮化、Staudinger还原、Jurjew反应和高度非对映选择性催化加氢。这些步骤促进了最终氨基和n -乙酰氨基吲哚嗪的高效和立体选择性合成。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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