American Chemical Society
jo8b01634_si_001.pdf (13.12 MB)

Unified Total Synthesis, Stereostructural Elucidation, and Biological Evaluation of Sarcophytonolides

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journal contribution
posted on 2018-08-09, 00:00 authored by Hiroyoshi Takamura, Takahiro Kikuchi, Kohei Iwamoto, Eiji Nakao, Naoki Harada, Taichi Otsu, Noriyuki Endo, Yuji Fukuda, Osamu Ohno, Kiyotake Suenaga, Yue-Wei Guo, Isao Kadota
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 SmI2-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.