A Novel Approach to the Tetracyclic Frameworks of Anislactone-type Sesquiterpenoids

IF 4.6 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2024-06-26 DOI:10.1039/d4qo00915k
Long He, Xiaocheng Zhang, Sen Li, Xuexue Tian, Yimeng Han, Haitao Xie, Weiqing Xie
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Abstract

Herein, we present a novel approach to construct the A-B-C-D ring system of anislactone-type sesquiterpenoids. This innovative strategy involves a H2O2-mediated oxidative ring contraction reaction to form a 5/5 fused skeleton, while simultaneously generating contiguous quaternary carbon centers (CQCCs). Additionally, the γ-lactones (A- and D- rings) are assembled through Pummerer reaction initiated cyclization and sequential Mukaiyama hydration/translactonization, respectively. Despite our efforts to introduce a hydroxyl group at C7 via C-H oxidation, these endeavors ultimately proved unsuccessful.
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研究茴香内酯类四环框架的新方法
在此,我们提出了一种构建苯甲内酯类倍半萜 A-B-C-D 环系统的新方法。这种创新策略涉及 H2O2- 介导的氧化缩环反应,以形成 5/5 融合骨架,同时生成连续的季碳中心 (CQCC)。此外,γ-内酯(A 环和 D 环)分别通过普默尔反应引发的环化和顺序的向山水合/反式内酯化组装而成。尽管我们努力通过 C-H 氧化在 C7 处引入羟基,但这些努力最终都没有成功。
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来源期刊
Organic Chemistry Frontiers
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.
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