α- n -邻苯二胺氧异丁酸介导的脱氧芳基化：丙烯烯A和丙烯烯B的全合成

IF 7.6 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chemical Science Pub Date : 2025-04-25 DOI:10.1039/d5sc00341e

Young Eum Hyun, Jeonguk Kweon, Thi Hieu Linh Phan, Dongwook Kim, Sunkyu Han

{"title":"α- n -邻苯二胺氧异丁酸介导的脱氧芳基化：丙烯烯A和丙烯烯B的全合成","authors":"Young Eum Hyun, Jeonguk Kweon, Thi Hieu Linh Phan, Dongwook Kim, Sunkyu Han","doi":"10.1039/d5sc00341e","DOIUrl":null,"url":null,"abstract":"Inspired by our biosynthetic hypothesis for 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. Alternatively, we designed 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 and B, as well as O7′-methyllacinilene E.","PeriodicalId":9909,"journal":{"name":"Chemical Science","volume":"14 1","pages":""},"PeriodicalIF":7.6000,"publicationDate":"2025-04-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"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, Sunkyu Han\",\"doi\":\"10.1039/d5sc00341e\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Inspired by our biosynthetic hypothesis for 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. Alternatively, we designed 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 and B, as well as O7′-methyllacinilene E.\",\"PeriodicalId\":9909,\"journal\":{\"name\":\"Chemical Science\",\"volume\":\"14 1\",\"pages\":\"\"},\"PeriodicalIF\":7.6000,\"publicationDate\":\"2025-04-25\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemical Science\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d5sc00341e\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Science","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/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

摘要

受alanense A的生物合成假说的启发，我们开发了两种不同的方法来对α- n -邻苯二甲酸二氧异丁酸酯（NPIB）进行脱氧芳基化，它们是由相邻或与羰基部分共轭的羟基衍生而来的。一种方法利用光氧化还原催化来实现自由基介导的芳基化反应。另外，我们设计了一种酸介导的芳基化方法，通过阳离子中间体进行。酸介导的方法成功地应用于丙烯酶A和丙烯酶B的全合成，以及O7 ' -甲基lacinilene E。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

α-N-Phthalimido-Oxy Isobutyrate-Mediated Deoxygenative Arylation: Total Synthesis of Alanenses A and B

Inspired by our biosynthetic hypothesis for 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. Alternatively, we designed 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 and B, as well as O7′-methyllacinilene E.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Chemical Science CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

4.80%

发文量

1352

审稿时长

2.1 months

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.