Niklāvs Ūdris , Rebeka Ločmele , Juris Pelšs , Anastasija Ture , Guna Sakaine , Artis Kinēns , Gints Smits
{"title":"Enantiopure piperidines via stereoselective Ireland–Claisen rearrangement: entry into corynanthe alkaloids†","authors":"Niklāvs Ūdris , Rebeka Ločmele , Juris Pelšs , Anastasija Ture , Guna Sakaine , Artis Kinēns , Gints Smits","doi":"10.1039/d4qo02235a","DOIUrl":null,"url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 6","pages":"Pages 1945-1950"},"PeriodicalIF":0.0000,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412925000403","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
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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