通过 1,4-Oxazinone 中间体的环加成/环转化合成瓜吡啶生物碱 Rupestine M 和 L。

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Synthesis-Stuttgart Pub Date : 2023-08-01 Epub Date: 2023-02-02 DOI:10.1055/s-0042-1751413

Jonathan R Scheerer, Ella B Leeth, Jennifer A Sprow

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引用次数: 0

摘要

研究人员开发了一种制备 1,4-恶嗪酮中间体的新方法，该方法基于 β-氨基醇与缺电子炔烃前体的偶氮共轭加成反应。从(-)-香茅醛开始，从而已知了 C5 立体中心的构型，并根据光学旋转提出了天然芦贝碱 L 的修正绝对构型。

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Synthesis of Guaipyridine Alkaloids Rupestine M and L by Cycloaddition/Cycloreversion of an Intermediate 1,4-Oxazinone.

A new method to prepare 1,4-oxazinone intermediates was developed based on aza-conjugate addition of β-amino alcohols to electron-deficient alkyne precursors. A tandem intramolecular cycloaddition/cycloreversion reaction sequence was evaluated, leading to the synthesis of the guaipyridine alkaloid natural products rupestine M and L. Starting from (-)-citronellal and thus a known configuration of the C5 stereocenter, a revised absolute configuration of natural rupestine L is suggested based on optical rotation.

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来源期刊

Synthesis-Stuttgart 化学-有机化学

CiteScore

4.50

自引率

7.70%

发文量

435

审稿时长

1 months

期刊介绍： SYNTHESIS is an international full-paper journal devoted to the advancement of the science of chemical synthesis. It covers all fields of organic chemistry involving synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines. SYNTHESIS provides dependable research results with detailed and reliable experimental procedures and full characterization of all important new products as well as scientific primary data.