| ID | 56205 |
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| Author |
Takamura, Hiroyoshi
Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University
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Fujiwara, Takayuki
Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University
Kawakubo, Yohei
Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University
Kadota, Isao
Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University
Uemura, Daisuke
Department of Chemistry, Faculty of Science, Kanagawa University
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| Abstract | Stereoselective and streamlined synthesis of the proposed C79-C104 fragment 2 of symbiodinolide (1), a polyol marine natural product with a molecular weight of 2860, was achieved. In the synthetic route, the proposed C79-C104 fragment 2 was synthesized by utilizing a Julia-Kocienski olefination and subsequent Sharpless asymmetric dihydroxylation as key transformations in a convergent manner. Detailed comparison of the 13 C NMR chemical shifts between the natural product and the synthetic C79-C104 fragment 2 revealed that the stereostructure at the C91-C99 carbon chain moiety of symbiodinolide (1) should be reinvestigated.
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| Keywords | macrocycles
natural products
polyols
stereoselective synthesis
structure elucidation
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| Note | This is an article published by Wiley-VCH
We appreciate JGC-S Scholarship Foundation, The Naito Foundation, The Sumitomo Foundation, and The Uehara Memorial Foundation for their financial supports.
This research was supported by a Grant-in Aid for Scientific Research (No. 24710250) from the Japan Society for the Promotion of Science (JSPS)
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| Published Date | 2016-02
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| Publication Title |
Chemistry - A European Journal
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| Volume | volume22
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| Issue | issue6
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| Publisher | Wiley-VCH
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| Start Page | 1979
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| End Page | 1983
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| ISSN | 0947-6539
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| NCID | AA11076269
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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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| Copyright Holders | https://creativecommons.org/licenses/by-nc-nd/4.0/deed.ja
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| File Version | author
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| Related Url | isVersionOf https://doi.org/10.1002/chem.201503880
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