Aza-Diels-Alder/intramolecular Heck cyclization approach to the tetrahydro-β-carboline skeleton of the ajmaline/sarpagine alkaloids

Jeffrey T. Kuethe, Audrey Wong, Ian W. Davies, Paul J. Reider

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

The aza-Diels-Alder reactions of 2-iodo-3-indoleacetaldehydes in the presence of zinc triflate provides 2-(2-iodoindolylmethyl)-4-pyridones in high yield. Palladium-mediated intramolecular Heck cyclization gives access to the tetracyclic tetrahydro-β-carboline framework of the ajmaline/sarpagine alkaloids.

Original languageEnglish (US)
Pages (from-to)3871-3874
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number21
DOIs
StatePublished - May 20 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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