Synthesis of the heterocyclic core of martinelline and martinellic acid

Mark Hadden, Mark Nieuwenhuyzen, Daire Osborne, Paul J. Stevenson*, Norris Thompson, Andrew D. Walker

*Corresponding author for this work

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

A Povarov reaction, between an aromatic imine derived from cinnamaldehyde and a cyclic enamide, was employed to rapidly construct the tricyclic core of the alkaloids martinelline and martinellic acid. The cycloaddition was completely regioselective though the exo/endo selectivity was poor. The diastereoisomers were readily separated by flash chromatography and the relative stereochemistry of the exo-isomer confirmed by single crystal X-ray crystallography. This intermediate was converted to the central core of the aforementioned alkaloids in five additional synthetic operations.

Original languageEnglish
Pages (from-to)3977-3984
Number of pages8
JournalTetrahedron
Volume62
Issue number17
DOIs
Publication statusPublished - 24 Apr 2006

Keywords

  • Alkaloid
  • Imino Diels-Alder
  • Lewis acid catalysis
  • Martinellic acid
  • Martinelline
  • Povarov reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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