Synthesis of vinca alkaloids and related compounds. Part 105: Efficient convergent synthetic pathway to the ibophyllidine skeleton and synthesis of (±)-19-hydroxy-ibophyllidine and (±)-19-hydroxy-20-epiibophyllidine

Flórián Tóth, György Kalaus, István Greiner, Mária Kajtár-Peredy, Ágnes Gömöry, László Hazai, Csaba Szántay

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Starting from methyl-5-oxohexanoate we produced the appropriately functionalized aldehyde, which, after having been allowed to react with the tryptamine derivative in a [4+2] cycloaddition reaction as the final step, yielded the molecule containing a D-seco-aspidospermane skeleton. From the latter we could successfully produce a 1:1 mixture of protected epimers, the desilylation reaction of the protected molecules gave the alkaloids (±)-19-hydroxy-ibophyllidine and (±)-19-hydroxy-20-epiibophyllidine in good yield.

Original languageEnglish
Pages (from-to)12011-12016
Number of pages6
JournalTetrahedron
Volume62
Issue number51
DOIs
Publication statusPublished - Dec 18 2006

Keywords

  • 19-Hydroxy-20-epiibophyllidine
  • 19-Hydroxy-ibophyllidine
  • Indole alkaloids
  • Natural products

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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