金催化脱芳螺旋环化法制备红杜鹃烷L

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-02 DOI:10.1021/acs.orglett.5c01802

Emily A. Shimizu, Scott D. Rychnovsky

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引用次数: 0

摘要

本文首次从真菌棕榈红桃属（Rhodotus palmatus）中分离得到了一种全合成的红桃烷型萜类化合物红桃烷L。这种独特的三环支架含有螺旋[4.5]自行车具有抗真菌活性。关键步骤包括非对映选择性铜加成，金催化脱芳螺旋环化和分子内醛化。这是首次在全合成中应用催化控制的不对称脱芳螺旋环化反应。合成红杜鹃烷L共17步，为最长的线性序列。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis of Rhodocorane L Using Gold-Catalyzed Dearomative Spirocyclization

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Synthesis of Rhodocorane L Using Gold-Catalyzed Dearomative Spirocyclization

Reported herein is the first total synthesis of the acorane-type terpenoid rhodocorane L, isolated from the fungus Rhodotus palmatus. This unique tricyclic scaffold containing a spiro[4.5] bicycle has antifungal activity. Key steps include diastereoselective cuprate addition, gold-catalyzed dearomative spirocyclization, and intramolecular aldol. This is the first time that a catalyst-controlled asymmetric dearomative spirocyclization has been utilized in a total synthesis. Rhodocorane L was synthesized in 17 steps, as the longest linear sequence.

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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.