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

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-01-22 DOI:10.1039/d4qo02235a

Niklāvs Ūdris , Rebeka Ločmele , Juris Pelšs , Anastasija Ture , Guna Sakaine , Artis Kinēns , 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。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Enantiopure piperidines via stereoselective Ireland–Claisen rearrangement: entry into corynanthe alkaloids†

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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 : an international journal of organic chemistry

CiteScore

7.80

自引率

0.00%

发文量