（−）-氟素A和(−)-15′-外延氟素D的全合成

IF 7.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chemical Science Pub Date : 2024-12-12 DOI:10.1039/D4SC07525K

Seung Mo Seo, Dongwook Kim, Taewan Kim and Sunkyu Han

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引用次数: 0

摘要

Securinega生物碱以其独特的结构和神经可塑性诱导潜力而闻名，是治疗神经退行性疾病（如抑郁症和物质使用障碍（SUD））的有希望的候选者。在此，我们描述了基于Rauhut-Currier （RC）反应的两种二聚体securinega生物碱，(−)-flueggenine A和(−)-15 ' -epi-flueggenine d的全合成。关键步骤涉及一种新的还原Heck二聚化策略，利用硅烷基系链烯酮偶联伙伴来确保所需的反应性和立体选择性。这种二聚化方法，结合已建立的化学途径探索(−)-氟基因C和D，提供了一种全面的合成方法来获取所有已知的基于rc的低聚securinega生物碱。

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 (−)-flueggenine A and (−)-15′-epi-flueggenine D†

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Total synthesis of (−)-flueggenine A and (−)-15′-epi-flueggenine D†

Securinega alkaloids, known for their unique structures and neuroplasticity-inducing potential, are promising candidates for treating neurodegenerative diseases such as depression and substance use disorders (SUD). Herein, we delineate the total synthesis of two dimeric Rauhut–Currier (RC) reaction-based securinega alkaloids, (−)-flueggenine A and (−)-15′-epi-flueggenine D. The key step involved a novel reductive Heck dimerization strategy, utilizing a silyl-tethered enone coupling partner to ensure the desired reactivity and stereoselectivity. This dimerization method, combined with established chemistry explored en route to (−)-flueggenines C and D, offers a comprehensive synthetic approach for accessing all known RC-based oligomeric securinega alkaloids.

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来源期刊

Chemical Science CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

4.80%

发文量

1352

审稿时长

2.1 months

期刊介绍： Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.