通过立体选择爱尔兰-克莱森重排的对映纯胡椒碱：进入香堇生物碱

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-01-21 DOI:10.1039/d4qo02235a

Niklāvs Ūdris, Rebeka Ločmele, J. Pelss, Anastasija Ture, Guna Sakaine, Artis Kinens, Gints Smits

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引用次数: 0

摘要

一种完全立体发散的非手性内酯的ireland - clisen重排已经被开发出来，可以获得3,4-二取代哌啶和吡咯烷的所有四种可能的立体异构体。在美喹烯酯和具有心脏保护作用的吲哚类生物碱西sirikine和二氢西sirikine的全合成中，已经展示了这些构建块的效用。

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Enantiopure Piperidines via Stereoselective Ireland-Claisen Rearrangement: Entry into Corynanthe Alkaloids

A fully stereo-divergent Ireland-Claisen rearrangement of achiral lactones has been developed enabling access to all four possible stereoisomers of 3,4-disubstituted piperidines and pyrrolidines. The utility of these building blocks has been showcased in the total synthesis of meroquinene ester and cardioprotective indole alkaloids sitsirikine and dihydrositsirikine.

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.