（−）-异戊烯烯的正式全合成及(+)-4-外异戊烯烯醇立体发散分子内烷基化结构的测定

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-24 DOI:10.1021/acs.orglett.5c00480

Youngjik Park, Hongjun Jang, Soo Yeon Kwak, Seongju Lim, Dongjoo Lee, Hyoungsu Kim, Deukjoon Kim

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引用次数: 0

摘要

本文描述了(−)-异aurallene(1)的正式全合成和通过高度立体发散的分子内酰胺烯醇酯烷基化（IAEA）策略确定新分离的(+)-4-外异aurallene(2)的结构。通过将共同中间体5分别置于非螯合控制和螯合控制的IAEA中，实现了α，α′-反式thf 3和α，α′-顺式thf 4的高度立体选择性构建。前一种方案大大提高了先前通过分子内腈阴离子烷基化（INAA）构建α，α ' -反式thf环的中等立体选择性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Formal Total Synthesis of (−)-Isolaurallene and Structure Determination of (+)-4-epi-Isolaurallene via Stereodivergent Intramolecular Amide Enolate Alkylation

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Formal Total Synthesis of (−)-Isolaurallene and Structure Determination of (+)-4-epi-Isolaurallene via Stereodivergent Intramolecular Amide Enolate Alkylation

Described herein are the formal total syntheses of (−)-isolaurallene (1) and structure determination of newly isolated (+)-4-epi-isolaurallene (2) via a highly stereodivergent intramolecular amide enolate alkylation (IAEA) strategy. Highly stereoselective constructions of α,α′-trans-THF 3 and α,α′-cis-THF 4 were accomplished by subjecting common intermediate 5 to non-chelate-controlled and chelate-controlled IAEA, respectively. The former protocol greatly improves the moderate stereoselectivity previously observed in constructing α,α′-trans-THF rings via intramolecular nitrile anion alkylation (INAA).

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.