Regioselective domino metathesis of 7-oxanorbornenes and its application to the synthesis of biologically active glutamate analogues

Minoru Ikoma, Masato Oikawa*, Martin B. Gill, Geoffrey T. Swanson, Ryuichi Sakai, Keiko Shimamoto, Makoto Sasaki

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

A highly regioselective domino metathesis reaction of 7-oxanorbornene was developed that employed an intramolecular association of an amide carbonyl group to a ruthenium metal centre. By using this reaction, twelve glutamate analogues inspired by dysiherbaine were efficiently synthesized over 12-14 steps; one of the analogues exhibited bioactivity consistent with central nervous system depression.

Original languageEnglish (US)
Pages (from-to)5215-5220
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number31
DOIs
StatePublished - Nov 1 2008

Keywords

  • Combinatorial chemistry
  • Domino reactions
  • Metathesis
  • Nitrogen heterocycles
  • Oxygen heterocycles
  • Regioselectivity

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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