Formal Synthesis of Lobatamides A and C

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-17 DOI:10.1021/acs.orglett.5c0073910.1021/acs.orglett.5c00739

Yuki Nakahara, Takumi Fukuda, Ryo Fujii, Masaki Kanakogi, Hitoshi Ouchi, Fumihiko Yoshimura, Ryo Takita, Toshiyuki Kan, Makoto Inai* and Yoshitaka Hamashima*,

引用次数: 0

Abstract

Lobatamides, featuring a unique 15-membered dilactone core, are a family of marine natural products isolated from the tunicate Aplidium lobatum and exhibit inhibitory activity against mammalian vacuolar-type proton pump ATPase (V-ATPase). Herein, we report an alternative route to Sato’s intermediate, achieving formal syntheses of lobatamides A and C. Key steps include the palladium-catalyzed Suzuki–Miyaura coupling reaction to give a salicylic acid derivative containing a trisubstituted (Z)-olefin and the Nozaki–Hiyama–Takai–Kishi (NHTK) reaction to construct the 15-membered dilactone core.

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洛巴他胺A和C的正式合成

Lobatamides是一种从被囊动物lobatum中分离出来的海洋天然产物，具有独特的15元二内酯核，对哺乳动物液泡型质子泵atp酶（v - atp酶）具有抑制活性。本文中，我们报道了一条替代佐藤中间体的途径，实现了lobatamides A和c的正式合成。关键步骤包括钯催化的Suzuki-Miyaura偶联反应，得到含有三取代(Z)-烯烃的水杨酸衍生物，以及Nozaki-Hiyama-Takai-Kishi （NHTK）反应，构建15元二内酯核心。

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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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.