立体选择性烯醇酸烷基化法合成丙烯醚B。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-09-20 DOI:10.1021/acs.joc.5c01409

Jun-ya Matsumoto, , , Shunsuke Sueki, , , Kosho Makino*, , and , Masahiro Anada*,

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引用次数: 0

摘要

（±）-alanense B是一种独特的、前所未有的2-芳基取代的丁二烷型倍半萜类化合物，在原代培养的新皮层神经元中表现出自发的钙通道振荡。利用KHMDS在1,2-二甲氧基乙烷中进行分子内frieel - crafts酰化和烯酸酯甲基化，得到了具有完全非对映选择性的C2位置上具有季立体中心的五取代1-四酮。在DDQ氧化之前，三个酚甲基醚的裂解是达到最终产品所必需的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Total Synthesis of Alanense B via Stereoselective Enolate Alkylation

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Total Synthesis of Alanense B via Stereoselective Enolate Alkylation

A total synthesis of (±)-alanense B, a unique and unprecedented 2-aryl substituted cadinane-type sesquiterpenoid that exhibits spontaneous calcium channel oscillations in primary cultured neocortical neurons, has been accomplished. Intramolecular Friedel–Crafts acylation and enolate methylation using KHMDS in 1,2-dimethoxyethane yielded the pentasubstituted 1-tetralone bearing a quaternary stereogenic center at the C2 position with complete diastereoselectivity. Cleavage of three phenolic methyl ethers prior to DDQ oxidation was essential for reaching the final product.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.