不对称氢化和Aza-Wacker环化制备核心螺旋环戊烷-1,2′-吲哚啉结构的对映选择性全合成(−)-缬沙脒

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-22 DOI:10.1021/acs.orglett.5c0161510.1021/acs.orglett.5c01615

Fan Yang, Xia-Lin Wang, Feng-Kai Zhao, Huai-Yu Bin and Jian-Hua Xie*,

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引用次数: 0

摘要

描述了(−)-缬沙脒的对映选择性全合成，将不对称氢化与aza-Wacker环化相结合，形成手性旋环戊烷-1,2 ' -吲哚啉。采用分子内Stetter反应和烷基化反应构建了以手性季碳为中心的四环骨架。施密特重排和分子内醛缩合促进了D环和E环的形成。该合成由外环烯酮酯合成(−)-缬沙脒，共14步，总产率为4.2%。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Enantioselective Total Synthesis of (−)-Vallesamidine Enabled by Asymmetric Hydrogenation and Aza-Wacker Cyclization to Construct the Core Spirocyclopentane-1,2′-indoline Structure

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Enantioselective Total Synthesis of (−)-Vallesamidine Enabled by Asymmetric Hydrogenation and Aza-Wacker Cyclization to Construct the Core Spirocyclopentane-1,2′-indoline Structure

An enantioselective total synthesis of (−)-vallesamidine is described, integrating asymmetric hydrogenation with aza-Wacker cyclization to form the chiral spirocyclopentane-1,2′-indoline. Intramolecular Stetter reaction and alkylation are employed to construct a tetracyclic framework featuring a chiral quaternary carbon center. Schmidt rearrangement and intramolecular aldol condensation facilitate the formation of the D and E rings. This synthesis achieves (−)-vallesamidine in 14 steps in an overall yield of 4.2% from an exocyclic enone ester.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.