Young Eum Hyun, Jeonguk Kweon, Thi Hieu Linh Phan, Dongwook Kim and Sunkyu Han
{"title":"α-N-phthalimido-oxy isobutyrate-mediated deoxygenative arylation: total synthesis of alanenses A and B†","authors":"Young Eum Hyun, Jeonguk Kweon, Thi Hieu Linh Phan, Dongwook Kim and Sunkyu Han","doi":"10.1039/D5SC00341E","DOIUrl":null,"url":null,"abstract":"<p >Inspired by a biosynthetic hypothesis of alanense A, we developed two distinct methods for the deoxygenative arylation of α-<em>N</em>-phthalimido-oxy isobutyrate (NPIB), derived from hydroxyl groups adjacent to or conjugated with a carbonyl moiety. One approach utilizes photoredox catalysis to achieve a radical-mediated arylation reaction. The other approach involves an acid-mediated arylation method that proceeds through a cationic intermediate. The acid-mediated approach was successfully applied to the total syntheses of alanenses A, B, and O7′-methyllacinilene E.</p>","PeriodicalId":9909,"journal":{"name":"Chemical Science","volume":" 22","pages":" 9943-9950"},"PeriodicalIF":7.4000,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/sc/d5sc00341e?page=search","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Science","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/sc/d5sc00341e","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Inspired by a biosynthetic hypothesis of alanense A, we developed two distinct methods for the deoxygenative arylation of α-N-phthalimido-oxy isobutyrate (NPIB), derived from hydroxyl groups adjacent to or conjugated with a carbonyl moiety. One approach utilizes photoredox catalysis to achieve a radical-mediated arylation reaction. The other approach involves an acid-mediated arylation method that proceeds through a cationic intermediate. The acid-mediated approach was successfully applied to the total syntheses of alanenses A, B, and O7′-methyllacinilene E.
期刊介绍：
Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
