Synthesis of Daucane Natural Products Enabled by a Gold(I)-Catalyzed Tandem Cycloisomerization/(4 + 3) Cycloaddition

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-02-27 DOI:10.1021/acs.orglett.4c04542
Àlex Martí, Helena Armengol-Relats, Anna Sadurní, Miquel À. Pérez-Puigdomènech, Antonio M. Echavarren
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Abstract

A divergent synthesis of three members of the daucane family of natural products is reported, enabled by a gold(I)-catalyzed cycloisomerization/formal (4 + 3) cycloaddition as the key step. The synthesis of penigrisacid A features a vanadium-catalyzed tandem epoxidation/SN2′ cyclization, whereas a Suárez radical cyclization enables the synthesis of aspterric acid. This work has also led to the reassignment of the structure of penigrisacid A as well as a short formal synthesis of schisanwilsonene A.

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本研究以金(I)催化的环异构化/形式(4 + 3)环加成为关键步骤,报道了一种不同的天然产物杜烷家族三个成员的合成方法。五味子酸 A 的合成采用了钒催化的串联环氧化/SN2′环化,而苏亚雷斯自由基环化则促成了天冬氨酸的合成。这项工作还重新确定了五味子酸 A 的结构,并对五味子烯 A 进行了简短的正式合成。
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来源期刊
Organic Letters
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.
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