Formal Synthesis of Lobatamides A and C

被引：0

作者：

Nakahara, Yuki ^{[1
]}

Fukuda, Takumi ^{[1
]}

Fujii, Ryo ^{[1
]}

Kanakogi, Masaki ^{[1
]}

Ouchi, Hitoshi ^{[1
]}

Yoshimura, Fumihiko ^{[1
]}

Takita, Ryo ^{[1
]}

Kan, Toshiyuki ^{[1
]}

Inai, Makoto ^{[1
]}

Hamashima, Yoshitaka ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Shizuoka 4228526, Japan

来源：

ORGANIC LETTERS | 2025年 / 27卷 / 12期

关键词：

CROSS-COUPLING REACTIONS; MARINE NATURAL-PRODUCTS; STEREOCHEMICAL ASSIGNMENT; CYTOTOXIC MACROLIDES; SECONDARY ALCOHOLS; OXIDATION; REAGENTS; CHLORIDE; ANALOGS;

D O I：

10.1021/acs.orglett.5c00739

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3066 / 3070

页数：5

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