Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid

Raku Watanabe, Nobuki Kato, Kengo Hayashi, Sho Tozawa, Yusuke Ogura, Shigefumi Kuwahara, Minoru Ueda

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient and stereoselective syntheses of all the possible stereoisomers of coronafacic acid (CFA) has been developed. The stereochemistries of C3a and C7a were controlled in a diastereoselective Diels-Alder type cycloaddition using a chiral auxiliary. CFA and 6-epi-CFA were synthesized by hydrogenation of a common intermediate. During the synthesis of 6-epi-CFA, we established that its cis-fused configuration is important for the introduction of C4-C5 double bond by dehydration. This report is the first practical synthesis of both 6-epi-CFA, and its enantiomer.

Original languageEnglish
Pages (from-to)1008-1017
Number of pages10
JournalChemistryOpen
Volume9
Issue number10
DOIs
Publication statusPublished - 2020 Oct 1

Keywords

  • coronatine
  • natural products
  • phytochemistry

ASJC Scopus subject areas

  • Chemistry(all)

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