Department of Chemistry, Graduate School of Natural Science and Technology , Okayama University , 3-1-1 Tsushimanaka, Kita-ku , Okayama 700-8530 , Japan.
Himeji EcoTech Co., Ltd. , 841-49 Koh, Shirahama-cho , Himeji 672-8023 , Japan.
J Org Chem. 2018 Sep 21;83(18):11028-11056. doi: 10.1021/acs.joc.8b01634. Epub 2018 Aug 23.
Sarcophytonolides are cembranolide diterpenes isolated from the soft corals of genus Sarcophyton. Unified total synthesis of sarcophytonolides C, E, F, G, H, and J and isosarcophytonolide D was achieved. The synthetic routes feature NaHMDS- or SmI-mediated fragment coupling, alkoxycarbonylallylation, macrolactonization, and transannular ring-closing metathesis. These total syntheses led to the absolute configurational confirmation of sarcophytonolide H, elucidation of sarcophytonolides C, E, F, and G, and revision of sarcophytonolide J and isosarcophytonolide D. We also evaluated the antifouling activity and toxicity of the synthetic sarcophytonolides H and J and their analogues as well as the cytotoxicity of the synthetic sarcophytonolides and the key synthetic intermediates.
软珊瑚中的软珊瑚醇内酯二萜类化合物是从软珊瑚属中分离出来的。已经实现了软珊瑚醇内酯 C、E、F、G、H 和 J 以及异软珊瑚醇内酯 D 的统一全合成。这些合成路线的特点是 NaHMDS-或 SmI-介导的片段偶联、烷氧基羰酰基烯丙基化、大环内酯化和环间闭环复分解反应。这些全合成导致了软珊瑚醇内酯 H 的绝对构型确认、软珊瑚醇内酯 C、E、F 和 G 的阐明，以及软珊瑚醇内酯 J 和异软珊瑚醇内酯 D 的修订。我们还评估了合成的软珊瑚醇内酯 H 和 J 及其类似物的抗污活性和毒性，以及合成的软珊瑚醇内酯和关键合成中间体的细胞毒性。
