一种铑催化的 C-H 活化/环化方法，用于从一种共同的中间体全合成决明素 C 和 8-O-甲基决明素 A。

IF 2.9 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-10-02 DOI:10.1039/d4ob01122h

Didier F. Vargas , Santiago Fonzo , Sebastian O. Simonetti , Teodoro S. Kaufman , Enrique L. Larghi

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引用次数: 0

摘要

本报告从一个色满酮共同关键中间体出发，报告了三种简短高效的决明素 C 全合成方法。在其新戊酰基肟的铑催化下，采用 C-H 活化策略安装了吡啶环。中间产物的动力学实验和 DFT 计算有助于深入了解 CD3OD 中桂皮素 C 不同寻常的位点和立体特异性 H/D 交换。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

A rhodium-catalyzed C–H activation/cyclization approach toward the total syntheses of cassiarin C and 8-O-methylcassiarin A from a common intermediate†

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A rhodium-catalyzed C–H activation/cyclization approach toward the total syntheses of cassiarin C and 8-O-methylcassiarin A from a common intermediate†

Three short and efficient total syntheses of cassiarin C are reported, from a chromanone common key intermediate. A C–H activation strategy, under rhodium catalysis on its pivaloyl oxime, enabled the installation of the pyridine ring. Dehydrogenation of 8-O-methylcassiarin C afforded 8-O-methylcassiarin A. A kinetic experiment and DFT calculations of the intermediates helped to gain insight into the unusual site- and stereo-specific H/D exchange of cassiarin C in CD₃OD.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.