Yonglian Zhang, Chunrui Sun, Liangqin Guo, Kake Zhao, Frank Bennett, Yu-hong Lam, Qi Gao, Kyle E. Ruhl, Michael T. Pirnot, Marion H. Emmert, Kaspar Hollenstein, Michael J. Eddins, Hua-Poo Su, Guangxin Shao, Chaohui Song, Michael Man-Chu Lo, Feng Peng, Ji Qi, Brendan M. Crowley, John A. McCauley, Ian R. Price
{"title":"Highly Diastereoselective Access to Densely Functionalized Piperidine Cores of Influenza Endonuclease Inhibitors via a Metal-Free SN1 Approach","authors":"Yonglian Zhang, Chunrui Sun, Liangqin Guo, Kake Zhao, Frank Bennett, Yu-hong Lam, Qi Gao, Kyle E. Ruhl, Michael T. Pirnot, Marion H. Emmert, Kaspar Hollenstein, Michael J. Eddins, Hua-Poo Su, Guangxin Shao, Chaohui Song, Michael Man-Chu Lo, Feng Peng, Ji Qi, Brendan M. Crowley, John A. McCauley, Ian R. Price","doi":"10.1021/acs.joc.4c02379","DOIUrl":null,"url":null,"abstract":"A novel, highly diastereoselective, and metal-free synthesis of multisubstituted piperidines via an S<sub>N</sub>1 approach is reported in this study. The method allows for the preparation of highly functionalized compounds with exceptional diastereomeric selectivities and consistently reproducible yields. These compounds are of significant interest due to their remarkable biological activities toward influenza endonuclease.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"55 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02379","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A novel, highly diastereoselective, and metal-free synthesis of multisubstituted piperidines via an SN1 approach is reported in this study. The method allows for the preparation of highly functionalized compounds with exceptional diastereomeric selectivities and consistently reproducible yields. These compounds are of significant interest due to their remarkable biological activities toward influenza endonuclease.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.