Synthesis of the diaryl ether cores common to chrysophaentins A, E, and F

Anthony J. Brockway, Charles I. Grove, Maximillian E. Mahoney, Jared T. Shaw

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

The synthesis of the diaryl ether subunits of the marine natural products chrysophaentin A, E, and F is described. These natural products feature tetrasubstituted benzene rings with complex substitution patterns. The central strategy involves an S<inf>N</inf>Ar reaction between a complex phenol and a polysubstituted fluoronitrobenzene. Subsequent attempts to construct the unusual E-chloroalkene linkage through several different approaches are also disclosed.

Original languageEnglish (US)
Pages (from-to)3396-3401
Number of pages6
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
StatePublished - May 25 2015

Keywords

  • Chrysophaentin
  • Claisen
  • FtsZ
  • Natural product synthesis
  • S<inf>N</inf>Ar

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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    Brockway, A. J., Grove, C. I., Mahoney, M. E., & Shaw, J. T. (2015). Synthesis of the diaryl ether cores common to chrysophaentins A, E, and F. Tetrahedron Letters, 56(23), 3396-3401. https://doi.org/10.1016/j.tetlet.2015.01.073