論文

査読有り 筆頭著者 国際誌
2020年1月10日

Stereoselective Synthesis of the Tricyclic Core of (−)-Callophycoic Acid A

The Journal of Organic Chemistry
  • Akihiro Sakama
  • ,
  • Rika Kameshima
  • ,
  • Yuko Motohashi
  • ,
  • Wataru Sumida
  • ,
  • Yuta Unno
  • ,
  • Keisuke Yoshida
  • ,
  • Akihiro Ogura
  • ,
  • Ken-ichi Takao

85
5
開始ページ
3245
終了ページ
3264
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1021/acs.joc.9b03114
出版者・発行元
American Chemical Society

Two stereocontrolled routes to the tricyclic core of (−)-callophycoic acid A are described. Our synthetic strategy relied on stereoselective allylboration using a new allylboronate reagent to construct the all-carbon quaternary stereocenter in the core, followed by efficient radical cyclization or palladium-catalyzed reductive cyclization to form its multisubstituted cyclohexane ring. The tetrahydrooxepin ring was constructed by intramolecular etheration. This study provides the first method for the stereoselective synthesis of the characteristic tricyclic skeleton of callophycoic acids.

リンク情報
DOI
https://doi.org/10.1021/acs.joc.9b03114
URL
https://pubs.acs.org/doi/10.1021/acs.joc.9b03114
ID情報
  • DOI : 10.1021/acs.joc.9b03114
  • ISSN : 1520-6904
  • ORCIDのPut Code : 68009706

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