Stereoselective synthesis of (+)-2-deoxyolivin based on cycloaddition reaction between the homophthalic anhydride and the chiral cyclohexenone derivative

Yoshinari Haruta, Kazumitsu Onizuka, Kyouichi Watanabe, Kyoko Kono, Akihiro Nohara, Kenichi Kubota, Shuhei Imoto, Shigeki Sasaki

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The olivomycins are representative antitumor antibiotics in the aureolic family of the compounds, which contains the tricyclic aglycon core, olivin. In this study, we established the efficient synthesis of the anthracenone core skeleton based on a cycloaddition reaction between the homophthalic anhydride and the chiral cyclohexenone derivatives, which is promoted by the combined use of molecular sieves, proton sponge, and a Lewis acid. The cyclohexenone with four chiral centers was synthesized by asymmetric and diastereoselective reactions, and was subjected to the cycloaddition reaction with a homophthalic anhydride followed by a sequence of reactions to accomplish stereoselective synthesis of (+)-2-deoxyolivin.

Original languageEnglish
Pages (from-to)7211-7218
Number of pages8
JournalTetrahedron
Volume64
Issue number30-31
DOIs
Publication statusPublished - 2008 Jul 21
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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