Towards the total synthesis of mandelalide B: construction of the tetrahydrofuran/α-hydroxyl lactone fragment†

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-09-10 DOI:10.1039/D4QO01433B

Jia-Lei Yan, Jie Yu, Yingying Cheng, Mingze Yang, Zhengshuang Xu and Tao Ye

引用次数: 0

Abstract

The synthesis of the tetrahydrofuran/α-hydroxyl lactone fragment of mandelalide B has been achieved in a concise and highly stereoselective manner. The key steps in our synthesis are a mild Horner–Wadsworth–Emmons olefination to create the key carboxylate containing olefin, and a highly stereospecific iodine induced cyclization to construct the α-hydroxyl lactone moiety.

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实现曼德拉内酯 B 的全合成：构建四氢呋喃/α-羟基内酯片段

我们以简洁和高度立体选择性的方式合成了曼德拉内酯 B 的四氢呋喃/α-羟基内酯片段。我们合成的关键步骤是通过温和的 Horner-Wadsworth-Emmons 烯化反应生成含有烯烃的关键羧酸酯，并通过高度立体特异性的碘诱导环化反应构建出 α-羟基内酯分子。

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

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.