Synthesis of vinca alkaloids and related compounds. Part 108: Efficient convergent synthetic pathway to the ibophyllidine skeleton IV. First synthesis of (±)-18-hydroxy-20-epiibophyllidine

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

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The first total synthesis of the pentacyclic alkaloid (±)-18-hydroxy-20-epiibophyllidine was realized via an efficient preparation of the d-seco-pseudoaspidospermane molecule. The key step of the sequence involves an intramolecular [4+2] cycloaddition reaction of the dihydrosecodine intermediate, which was built up from the reaction of a tryptamine derivative with an aldehyde-ester. After full epimerization, the intramolecular N-alkylation of the tetracyclic ester gave the pentacyclic compound. Reduction of the latter molecule led to the title compound.

Original languageEnglish
Pages (from-to)7823-7827
Number of pages5
JournalTetrahedron
Volume63
Issue number33
DOIs
Publication statusPublished - Aug 13 2007

Keywords

  • 18-Hydroxy-20-epiibophyllidine
  • Deethylibophyllidine
  • Ibophyllidine
  • Indole alkaloids
  • Natural products

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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