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

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)3245-3264
Number of pages20
JournalJournal of Organic Chemistry
Volume85
Issue number5
DOIs
Publication statusPublished - 2020 Mar 6

ASJC Scopus subject areas

  • Organic Chemistry

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    Sakama, A., Kameshima, R., Motohashi, Y., Sumida, W., Unno, Y., Yoshida, K., Ogura, A., & Takao, K. I. (2020). Stereoselective Synthesis of the Tricyclic Core of (-)-Callophycoic Acid A. Journal of Organic Chemistry, 85(5), 3245-3264. https://doi.org/10.1021/acs.joc.9b03114