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ID 56205
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Author
Takamura, Hiroyoshi Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University
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
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.
Keywords
macrocycles
natural products
polyols
stereoselective synthesis
structure elucidation
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)
Published Date
2016-02
Publication Title
Chemistry - A European Journal
Volume
volume22
Issue
issue6
Publisher
Wiley-VCH
Start Page
1979
End Page
1983
ISSN
0947-6539
NCID
AA11076269
Content Type
Journal Article
language
英語
OAI-PMH Set
岡山大学
Copyright Holders
https://creativecommons.org/licenses/by-nc-nd/4.0/deed.ja
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isVersionOf https://doi.org/10.1002/chem.201503880