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

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

引用次数: 0

Abstract

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.

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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

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。

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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.