| ID | 56663 |
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| Author |
Takamura, Hiroyoshi
Department of Chemistry, Graduate School of Natural Science and Technology , Okayama University
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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
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| 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.
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| Note | This is an Accepted Manuscript of an article published by American Chemical Society
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| Published Date | 2018-08-09
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| Publication Title |
The Journal of Organic Chemistry
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| Volume | volume83
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| Issue | issue18
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| Publisher | American Chemical Society
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| Start Page | 11028
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| End Page | 11056
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| ISSN | 0022-3263
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| NCID | AA00704100
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| Content Type |
Journal Article
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| language |
English
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| OAI-PMH Set |
岡山大学
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| File Version | author
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| Web of Science KeyUT | |
| Related Url | isVersionOf https://doi.org/10.1021/acs.joc.8b01634
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