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ID 56663
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Takamura, Hiroyoshi Department of Chemistry, Graduate School of Natural Science and Technology , Okayama University
Kikuchi, Takahiro Department of Chemistry, Graduate School of Natural Science and Technology , Okayama University
Iwamoto, Kohei Department of Chemistry, Graduate School of Natural Science and Technology , Okayama University
Nakao, Eiji Department of Chemistry, Graduate School of Natural Science and Technology , Okayama University
Harada, Naoki Department of Chemistry, Graduate School of Natural Science and Technology , Okayama University
Otsu, Taichi Department of Chemistry, Graduate School of Natural Science and Technology , Okayama University
Endo, Noriyuki Himeji EcoTech Co., Ltd.
Fukuda, Yuji Himeji EcoTech Co., Ltd.
Ohno, Osamu Department of Chemistry and Life Science, School of Advanced Engineering , Kogakuin University
Suenaga, Kiyotake Department of Chemistry, Faculty of Science and Technology , Keio University
Guo, Yue-Wei Shanghai Institute of Materia Medica , Chinese Academy of Sciences
Kadota, Isao Department of Chemistry, Graduate School of Natural Science and Technology , Okayama University
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.
Note
This is an Accepted Manuscript of an article published by American Chemical Society
Published Date
2018-08-09
Publication Title
The Journal of Organic Chemistry
Volume
volume83
Issue
issue18
Publisher
American Chemical Society
Start Page
11028
End Page
11056
ISSN
0022-3263
NCID
AA00704100
Content Type
Journal Article
language
英語
OAI-PMH Set
岡山大学
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isVersionOf https://doi.org/10.1021/acs.joc.8b01634