一种聚类合成phragmalin型类柠檬素的方法：thigranatin P的全合成

IF 15.6 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Journal of the American Chemical Society Pub Date : 2025-09-26 DOI:10.1021/jacs.5c13081

Jaehoo Lee, Spencer C. Davis, Amber Sheu, Jacqueline W. Gu, Timothy R. Newhouse

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引用次数: 0

摘要

在此，我们报道了红卡松素M和L和苔格兰素P的全合成，这是拓扑结构复杂的phragmalin型柠檬素，后者对人妊娠X受体（hPXR）具有强烈的激动作用。一个关键的转化是smi2介导的醛和烯烃的还原偶联，构建了phragmalin天然产物特征的三环[3.3.12,10.11,4]癸烷框架。该合成的特点是通过适当的加成，膨胀和分子内Heck反应序列战略性地收敛了phragmalin核心结构的构建。该途径为合成结构多样的phragmalin类似物提供了一个多功能的平台，为未来的生物学研究提供了基础。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

A Convergent Approach to Phragmalin-Type Limonoids: Total Synthesis of Thaigranatin P

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A Convergent Approach to Phragmalin-Type Limonoids: Total Synthesis of Thaigranatin P

Herein, we report the total synthesis of erythrocarpines M and L and thaigranatin P, topologically complex phragmalin-type limonoids, the latter exhibiting potent agonism on the human pregnane X receptor (hPXR). A key transformation is a SmI₂-mediated reductive coupling of an aldehyde and an alkene, which constructs the signature tricyclo[3.3.1^2,10.1^1,4]decane framework characteristic of phragmalin natural products. The synthesis features a strategically convergent construction of the phragmalin core structure via a cuprate addition, triflation, and intramolecular Heck reaction sequence. This route offers a versatile platform for the synthesis of structurally diverse phragmalin analogs for future biological investigation.

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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.