Synthesis of the heterocyclic core of the alkaloids martinelline and martinellic acid

M. Hadden, Mark Nieuwenhuyzen, D. Osborne, Paul Stevenson, N. Thompson

Research output: Contribution to journalArticlepeer-review

54 Citations (Scopus)

Abstract

The tricyclic core of martinelline and martinellic acid was rapidly assembled utilising an imino Diels-Alder reaction of an imine derived from cinnamaldehyde with a cyclic enamide. The cycloaddition was completely regioselective though the exo endo selectivity was poor. These diastercoisomers 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. (C) 2001 Elsevier Science Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)6417-6419
Number of pages3
JournalTetrahedron Letters, ISSN
Volume42
Issue number36
Publication statusPublished - 03 Sept 2001

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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