Synthesis of vinca alkaloids and related compounds. part 109. An intramolecular [4+2] cycloaddition mediated biomimetic synthesis of (±)-iboxyphylline

Flórián Tóth, György Kalaus, Gergely Pipa, István Greiner, A. Szöllösy, Attila Rill, A. Gömöry, László Hazai, Csaba Szántay

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The pentacyclic alkaloid 1 could be synthesized by an intramolecular [4+2] cycloaddition reaction of intermediate 11, which had been obtained from tryptamine derivative 4 and aldehyde 5. After full epimerization of 13 the cyclization reaction furnished a mixture of 14a and 14b. Separation of the stereoisomers 14a and 14b and subsequent reduction with LiAIH4 resulted in (+)-iboxyphylline (14a -1) and its epimer, (+)-20-epiiboxyphylline (14b -+ 15).

Original languageEnglish
Pages (from-to)65-76
Number of pages12
JournalHeterocycles
Volume75
Issue number1
DOIs
Publication statusPublished - Jan 1 2008

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Vinca Alkaloids
Biomimetics
Stereoisomerism
Cycloaddition
Cyclization
Cycloaddition Reaction
Alkaloids
Aldehydes
Derivatives
tryptamine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of vinca alkaloids and related compounds. part 109. An intramolecular [4+2] cycloaddition mediated biomimetic synthesis of (±)-iboxyphylline. / Tóth, Flórián; Kalaus, György; Pipa, Gergely; Greiner, István; Szöllösy, A.; Rill, Attila; Gömöry, A.; Hazai, László; Szántay, Csaba.

In: Heterocycles, Vol. 75, No. 1, 01.01.2008, p. 65-76.

Research output: Contribution to journalArticle

Tóth, Flórián ; Kalaus, György ; Pipa, Gergely ; Greiner, István ; Szöllösy, A. ; Rill, Attila ; Gömöry, A. ; Hazai, László ; Szántay, Csaba. / Synthesis of vinca alkaloids and related compounds. part 109. An intramolecular [4+2] cycloaddition mediated biomimetic synthesis of (±)-iboxyphylline. In: Heterocycles. 2008 ; Vol. 75, No. 1. pp. 65-76.
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