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

Akihiro Sakama, Rika Kameshima, Yuko Motohashi, Wataru Sumida, Yuta Unno, Keisuke Yoshida, Akihiro Ogura, Ken Ichi Takao

研究成果: Article査読

1 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)3245-3264
ページ数20
ジャーナルJournal of Organic Chemistry
85
5
DOI
出版ステータスPublished - 2020 3 6

ASJC Scopus subject areas

  • Organic Chemistry

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