通过后期溴螺环化无保护基团全合成β-莱万特内酯

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-13 Epub Date: 2024-11-28 DOI:10.1021/acs.orglett.4c03542

Saubhik Ghosh, Shrestha Chatterjee, Samik Nanda

引用次数: 0

摘要

我们描述了一种通过反式萘烷附加γ-亚烷基丁烯内酯的偶然溴-螺环化反应，简便地不对称全合成天然[5,5]-氧杂天冬内酯β-相关烯内酯的方法。γ-亚烷基丁烯内酯的核心是通过 "Pd-Cu "双金属级联内酯化反应与适当官能化的对映纯炔烃构建而成的。(+)-Sclareolide 用作手性池起始材料，以获得所需的炔。

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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Protecting-Group Free Total Synthesis of β-Levantenolide through Late Stage Bromo-Spirocyclization.

We describe a concise asymmetric total synthesis of naturally occurring [5,5]-oxaspirolactone β-levantenolide through an adventitious bromo-spirocyclization reaction of a trans-decalin appended γ-alkylidenebutenolide. The γ-alkylidenebutenolide core was constructed through "Pd-Cu" bimetallic cascade lactonization reaction of properly functionalized enantiopure alkyne. (+)-Sclareolide was used as a chiral pool starting material to access the desired alkyne.

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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.