四环吲哚类化合物的简易方法：吲哚与n -取代环丁烷的高度非对映选择性[4+2]环化

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2024-12-30 DOI:10.1021/acs.joc.4c0250910.1021/acs.joc.4c02509

Peng-Juan Li, Xiao-Kang Kuang, Jun Zhu, Yong Tang and Lijia Wang*,

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引用次数: 0

摘要

提出了一种新的立体选择性[4+2]环化方法，通过吲哚与双环n -取代环丁烷反应生成四环吲哚。以Sc(OTf)3为催化剂，制备了一系列具有四个连续立体碳中心的四环吲哚类单对映体，产率≤86%。该反应为快速构建具有生物活性的天然产物如paucidirinine、deethylibophyllidine和ibophyllidine的核心结构提供了一种可行的方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

A Facile Approach to Tetracyclic Indolines: Highly Diastereoselective [4+2] Annulation of Indoles with Bicyclic N-Substituted Cyclobutanes

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A Facile Approach to Tetracyclic Indolines: Highly Diastereoselective [4+2] Annulation of Indoles with Bicyclic N-Substituted Cyclobutanes

A new stereoselective [4+2] annulation method for constructing tetracyclic indolines by reacting indoles with bicyclic N-substituted cyclobutanes has been developed. Using Sc(OTf)₃ as a catalyst, a series of tetracyclic indolines with four continued stereogenic carbon centers have been obtained in ≤86% yields as single diastereomers. This reaction offers an accessible way for the rapid construction of the core structures of biologically active natural products like paucidirinine, deethylibophyllidine, and ibophyllidine.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

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.