喹啉序贯脱芳法制备全苯胺内酯B

IF 15.6 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Journal of the American Chemical Society Pub Date : 2025-10-15 DOI:10.1021/jacs.5c14142

Bhawyanth Duvvuru, Myles W. Smith

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引用次数: 0

摘要

我们报道了第一个含环丁烷的石蒜生物碱酯内酯b的全合成。我们的方法利用顺序喹啉去芳化策略，使这种容易获得的杂芳香前体转化为三环n -酰基二氢吡啶酮中间体。广泛的研究旨在锻造签名环丁烷揭示了β-丙烯酸硅酯是关键的[2 + 2]光环加成反应的成功至关重要。进一步的官能团转化和最终的一锅甲基化/内酯化序列在20步内得到注释内酯B。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Total Synthesis of Annotinolide B via Sequential Quinoline Dearomatization

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Total Synthesis of Annotinolide B via Sequential Quinoline Dearomatization

We report the first total synthesis of the complex cyclobutane-containing Lycopodium alkaloid annotinolide B. Our approach leverages a sequential quinoline dearomatization strategy that enables the transformation of this readily accessible heteroaromatic precursor to a tricyclic N-acyl dihydropyridone intermediate. Extensive studies aimed at forging the signature cyclobutane revealed a β-silyl acrylate to be essential for the success of a key [2 + 2] photocycloaddition reaction. Further functional group transformations and a final one-pot methylation/lactonization sequence furnish annotinolide B in 20 steps.

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来源期刊

Journal of the American Chemical Society 化学-化学综合

CiteScore

24.40

自引率

6.00%

发文量

2398

审稿时长

1.6 months

期刊介绍： The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.