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ID 56202
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Takamura, Hiroyoshi Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University
Katsube, Tomoya Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University
Okamoto, Kazuki 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
Abstract
The first total synthesis of two possible diastereomers of natural 6-chlorotetrahydrofuran acetogenin 1 has been achieved. The synthetic route features 5-exo-tet cyclization, Z selective Wittig reaction and Julia olefination for the construction of conjugated diene and enyne moieties, and stereoselective chlorination. Comparison of their 1 H and 13 C NMR data and specific rotation with those of the natural product elucidated the absolute configuration of natural (-)-6-chlorotetrahydrofuran acetogenin 1.
Keywords
natural products
stereoselective synthesis
structure elucidation
tetrahydrofuran
total synthesis
Note
This is an article published by Wiley‐VCH
Published Date
2017-12-06
Publication Title
Chemistry - A European Journal
Volume
volume23
Issue
issue68
Publisher
Wiley‐VCH
Start Page
17191
End Page
17194
ISSN
09476539
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.201703234