Synthesis of 4α-hydroxy-2,5-diene-1-one framework toward jaborosalactone B

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-02-01 DOI:10.1016/j.tet.2024.134421

Qian Xu, Shunji Zhang, Yuting Li, Xiaoyu Xie, Ran Gao

引用次数: 0

Abstract

Herein we disclose the scalable synthesis of 4α-hydroxy-2,5-diene-1-one moiety, which is an essential fragment for the construction of withanolides such as Jaborosalactone B, starting from commercially available 21-hydroxy-20-methylpregn-4-en-3-one (BA) in 10 steps. The synthesis features a ¹O₂ involved Diels-Alder reaction with 1,3,5-triene to install the 1-hydroxy-4-one in A ring and a Ley's oxidation followed by β-elimination in one pot to furnish the 4α-hydroxy-2,5-diene-1-one moiety.

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在此，我们公开了以市售的 21-hydroxy-20-methylpregn-4-en-3-one (BA) 为原料，通过 10 个步骤合成 4α-羟基-2,5-二烯-1-酮分子的方法，该分子是制造硼砂内酯（如硼砂内酯 B）的重要片段。合成过程包括与 1,3,5- 三烯发生 1O2 参与的 Diels-Alder 反应，在 A 环中安装 1- 羟基-4-酮，以及莱氏氧化反应，然后在一锅中进行 β-消除反应，生成 4α- 羟基-2,5-二烯-1-酮分子。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.