Rapid Access to a Cyclobutane-Containing Skeleton Fused with Chromane through In(III)-Catalyzed Intramolecular Annulation of 5-Hydroxy Benzochromene.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-14 DOI:10.1021/acs.orglett.5c01352

Tao Jiang,FuJunyang Wu,Rong Xie,Yu-Lin Che,Hejiang Luo,Rong-Tao Li

引用次数: 0

Abstract

Intramolecular oxidative annulation of 5-hydroxy benzochromene via In(OTf)3 and DDQ catalysis, through an ortho-quinone methide radical intermediate, afforded various cyclobutane-containing products in good to excellent yields. This oxidative annulation pathway reveals great group tolerance and broad compatibility with benzochromene. In addition, this method exhibits an excellent ability to synthesize cyclobutane-containing products in gram-scale experiments, providing a novel approach to synthesize a series of natural products, such as cannabicyclol, isoeriobrucinol A, and ranhuadujuanine A.

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通过In（III）催化5-羟基苯并铬胺的分子内环反应快速获得含环丁烷与铬胺融合的骨架。

5-羟基苯并铬通过In(OTf)3和DDQ催化，通过邻醌甲基自由基中间体进行分子内氧化环化，得到了收率高至优异的各种含环丁烷的产物。这一氧化环化途径与苯并铬具有良好的基团耐受性和广泛的相容性。此外，该方法在克级实验中表现出良好的合成含环丁烷产物的能力，为合成大麻环酚、异戊三醇a、兰花都黄嘌呤a等一系列天然产物提供了新的途径。

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

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.