Synthesis of vinca alkaloids and related compounds. Part 110: A new synthetic method for the preparation of pandoline-type alkaloid-like molecules

Flórián Tóth, J. Oláh, György Kalaus, István Greiner, A. Szöllösy, A. Gömöry, László Hazai, Csaba Szántay

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A practicable synthesis of a pandoline-type alkaloid-like molecule is reported through an efficient preparation of carbinolamine ether intermediates (9a and 9b). The key step of the synthesis consists of an intramolecular cycloaddition of the secodine-type intermediate (2), which was formed from the tryptamine derivative (3) and lactol (4). The mechanism of the cycloaddition reaction was investigated by quantum chemical calculations and it was found to follow a step-wise mechanism involving a zwitterionic intermediate (15). By employing this strategy, other members of the family of pandoline alkaloids or alkaloid-like molecules could be synthesized by reacting the tryptamine derivative with appropriately functionalized aldehydes.

Original languageEnglish
Pages (from-to)7949-7955
Number of pages7
JournalTetrahedron
Volume64
Issue number34
DOIs
Publication statusPublished - Aug 18 2008

Fingerprint

Vinca Alkaloids
Alkaloids
Cycloaddition
Cycloaddition Reaction
Molecules
Derivatives
Aldehydes
Ether
tryptamine

Keywords

  • Ψ-Aspidospermane alkaloids
  • 19-Hydroxy-20-epipandoline
  • 20-Epipandoline
  • Diels-Alder reaction
  • Pandoline
  • Pandoline-like molecule
  • Reaction mechanism

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of vinca alkaloids and related compounds. Part 110 : A new synthetic method for the preparation of pandoline-type alkaloid-like molecules. / Tóth, Flórián; Oláh, J.; Kalaus, György; Greiner, István; Szöllösy, A.; Gömöry, A.; Hazai, László; Szántay, Csaba.

In: Tetrahedron, Vol. 64, No. 34, 18.08.2008, p. 7949-7955.

Research output: Contribution to journalArticle

Tóth, Flórián ; Oláh, J. ; Kalaus, György ; Greiner, István ; Szöllösy, A. ; Gömöry, A. ; Hazai, László ; Szántay, Csaba. / Synthesis of vinca alkaloids and related compounds. Part 110 : A new synthetic method for the preparation of pandoline-type alkaloid-like molecules. In: Tetrahedron. 2008 ; Vol. 64, No. 34. pp. 7949-7955.
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