意想不到的胺触发的fascaplysin及其衍生物的骨架修饰：快速获得δ，γ-biscarbolines。

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-01-16 DOI:10.1039/d4ob02014f

Zizhen Wang , Huanhuan Wang , Mei Xu , Liping Wang , Sheng Liu

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引用次数: 0

摘要

从fascaplysin框架直接构建生物碱iheyamine A的失败尝试导致了烷基化δ，γ-biscarboline衍生物的新合成方法的发现。在该方案易于操作的反应条件下，以中等到较高的收率制备了18种烷基化双碳烃。提出了一个意想不到的多米诺骨牌转化，涉及一个吡啶开环/氮杂电环化/氧化去甲酰基化序列。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Unexpected amine-triggered skeletal modification of fascaplysin and its derivatives: rapid access to δ,γ-biscarbolines†

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Unexpected amine-triggered skeletal modification of fascaplysin and its derivatives: rapid access to δ,γ-biscarbolines†

An unsuccessful attempt to directly construct alkaloid iheyamine A from a fascaplysin framework resulted in the discovery of a novel synthetic approach to alkylated δ,γ-biscarboline derivatives. With the easy-to-operate reaction conditions of this protocol, 18 alkylated biscarbolines have been prepared in moderate to good yields. An unexpected domino transformation was proposed to involve a pyridinium ring-opening/aza-electrocyclization/oxidative deformylation sequence.

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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.