Asymmetric Total Synthesis of Isolinearol Using Low-Valence Titanium and Evaluation of Its Inhibitory Activity against Mussel Byssal Thread Formation

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-25 DOI:10.1021/acs.orglett.4c04309

Tomoki Tsuruta, Keisuke Nishikawa, Yukika Yoshino, Daiki Osada, Tatsuhide Miwa, Kazumi Nimura, Takashi Kamada, Yoshiki Morimoto

引用次数: 0

Abstract

The asymmetric total synthesis of isolinearol, a seco-dolastane-type diterpenoid that inhibits byssal thread formation by mussels, has been achieved. In the synthesis, the key features include an intramolecular reductive nucleophilic addition using a low-valence titanium species and the direct installation of a ketone side chain. We evaluated their biological activities using the synthetic samples and found the novel inhibitory molecules with a simplified structure exhibit high inhibitory activities against byssus formation and low toxicities.

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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.