Synthesis of the bicyclic butenolide core of pallamolide A: a biomimetic approach†

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2024-08-30 Epub Date: 2024-09-09 DOI:10.1039/d4ob01380h
Grace J. Drummond , Phillip S. Grant , Alisha M. Geurts , Daniel P. Furkert , Margaret A. Brimble
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Abstract

Pallamolide A is a 7,8-seco-labdane terpenoid possessing a unique bicyclo[2.2.2]octane core and a spiro-butenolide moiety. A biomimetic synthesis of the bicyclic butenolide core over 10 steps is reported, featuring an unexpected autoxidation ring opening, and a vinylogous Mukaiyama aldol reaction which was spontaneously followed by an unusual intramolecular vinylogous aldol reaction to assemble the spiro-butenolide moiety and bicyclic core of pallamolide A.

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帕拉莫内酯 A 的双环丁烯内酯核心的合成:一种生物模拟方法
帕拉莫内酯 A 是一种 7,8-seco-labdane萜类化合物,具有独特的双环[2.2.2]辛烷核心和一个螺丁烯内酯分子。本研究报告通过 10 个步骤对双环丁烯内酯核心进行了生物模拟合成,其特点包括意想不到的自氧化开环和乙烯基 Mukaiyama 醛醇反应,该反应之后自发地发生了不寻常的分子内乙烯基醛醇反应,从而组装了帕拉莫内酯 A 的螺丁烯内酯分子和双环核心。
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来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
期刊介绍: Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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