Efficient construction of the core framework of lysidicin A via three Claisen rearrangements including a cascade reaction

Yusuke Ogura, Hidenori Watanabe

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A model compound (6) with the core skeleton of lysidicin A was synthesized as a racemate. The key step (8→7) includes three Claisen rearrangements of the triether with phloroglucinols; two of which rearranged in a cascade manner and the other was a simple rearrangement. This one-pot reaction enabled the introduction of three phloroglucinol units at the correct positions and makes the synthetic approach significantly efficient.

Original languageEnglish
Pages (from-to)3294-3296
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number25
DOIs
Publication statusPublished - 2010 Jun 23
Externally publishedYes

Keywords

  • Cascade reaction
  • Claisen rearrangement
  • Lysidicin A
  • Vasodilation activity

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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