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

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

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8 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)11028-11056
Number of pages29
JournalJournal of Organic Chemistry
Volume83
Issue number18
DOIs
Publication statusPublished - Sep 21 2018

ASJC Scopus subject areas

  • Organic Chemistry

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    Takamura, H., Kikuchi, T., Iwamoto, K., Nakao, E., Harada, N., Otsu, T., Endo, N., Fukuda, Y., Ohno, O., Suenaga, K., Guo, Y. W., & Kadota, I. (2018). Unified Total Synthesis, Stereostructural Elucidation, and Biological Evaluation of Sarcophytonolides. Journal of Organic Chemistry, 83(18), 11028-11056. https://doi.org/10.1021/acs.joc.8b01634