ID 56207
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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
Abstract
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.
Note
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).
Published Date
2015-02-27
Publication Title
The Journal of organic chemistry
Volume
volume80
Issue
issue6
Publisher
American Chemical Society
Start Page
3111
End Page
3123
ISSN
00223263
NCID
AA00704100
Content Type
Journal Article
language
英語
OAI-PMH Set
岡山大学
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DOI
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Related Url
isVersionOf https://doi.org/10.1021/acs.joc.5b00027