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, M. Kajtár-Peredy, A. Gömöry, László Hazai, Csaba Szántay

Research output: Contribution to journalArticle

6 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

Fingerprint

Vinca Alkaloids
Skeleton
Esters
Molecules
Cycloaddition
Alkylation
Cycloaddition Reaction
Alkaloids
Aldehydes
Derivatives
tryptamine

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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. / Tóth, Flórián; Kalaus, György; Horváth, Vajk Dániel; Greiner, István; Kajtár-Peredy, M.; Gömöry, A.; Hazai, László; Szántay, Csaba.

In: Tetrahedron, Vol. 63, No. 33, 13.08.2007, p. 7823-7827.

Research output: Contribution to journalArticle

Tóth, Flórián ; Kalaus, György ; Horváth, Vajk Dániel ; Greiner, István ; Kajtár-Peredy, M. ; Gömöry, A. ; Hazai, László ; Szántay, Csaba. / 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. In: Tetrahedron. 2007 ; Vol. 63, No. 33. pp. 7823-7827.
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