Synthesis of vinca alkaloids and related compounds, Part LXXXIX. Some unexpected reactions of compounds containing the D-seco-aspidospermane ring system

György Kalaus, Imre Juhász, Kinga Steinhauser, István Greiner, Mária Kajtár-Peredy, János Brlik, Lajos Szabó, Csaba Szántay

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4 Citations (Scopus)

Abstract

Interaction of the tryptamine derivative (3) with the formyl ester (4) gave (±)-20-deethyl-2,16-didehydro-14,16-bis(methoxycarbonyl)-3-phenyl-3,14- seco-20-epiaspidospermidine (7) instead of the expected acetal (6). The product of the reaction of 3 with the acetoacetic aldehyde derivative (5) was ethylene acetal of (±)-2,16-didehydro-16-methoxycarbonyl-3-phenyl-14,15- dinoraspidospermidin-19-one (8), it was readily convertible into the reactive intermediate (10). Further build-up starting from secondary amine (11) gave the N(4)-substituted derivatives, while 10 afforded products with unexpected structures. The reaction of 10 with acetic anhydride yielded different products depending on the reaction conditions.

Original languageEnglish
Pages (from-to)205-219
Number of pages15
JournalHeterocycles
Volume47
Issue number1
Publication statusPublished - dec. 1 1998

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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