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ID 56207
フルテキストURL
著者
Takamura, Hiroyoshi Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University
Wada, Hiroko Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University
Ogino, Mao 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
Kadota, Isao Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University
Uemura, Daisuke Department of Chemistry, Faculty of Science, Kanagawa University
抄録
Four possible diastereomers of the C1-C13 fragment of symbiodinolide, which were proposed by the stereostructural analysis of the degraded product, were synthesized in a stereodivergent and stereoselective manner. The key transformations were aldol reaction of methyl acetoacetate with the aldehyde, diastereoselective reduction of the resulting β-hydroxy ketone, and the stereoinversion at the C6 position. Comparison of the (1)H NMR data between the four synthetic products and the degraded product revealed the relative stereostructure of the C1-C13 fragment of symbiodinolide.
備考
This is an Accepted Manuscript of an article published by American Chemical Society
This research was supported by a Grant-in Aid for Scientific Research (No. 24710250) from the Japan Society for the Promotion of Science (JSPS).
発行日
2015-02-27
出版物タイトル
The Journal of organic chemistry
80巻
6号
出版者
American Chemical Society
開始ページ
3111
終了ページ
3123
ISSN
00223263
NCID
AA00704100
資料タイプ
学術雑誌論文
言語
English
OAI-PMH Set
岡山大学
論文のバージョン
author
PubMed ID
DOI
Web of Sience KeyUT
関連URL
isVersionOf https://doi.org/10.1021/acs.joc.5b00027