Synthesis of vinca alkaloids and related compounds, 73. Synthesis and ring transformations of deethylaspidospermane derivatives. Synthesis of (±)‐20‐deethyl‐3‐oxotabersonine

György Kalaus, Imre Juhász, István Greiner, M. Kajtár-Peredy, János Brlik, Lajos Szabó, Csaba Szántay

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The reaction of the key compound 14 with methyl 4‐formyl‐butanoate (9) or with 5‐benzoyloxypentanal (13) gave the D‐seco‐aspidospermane derivatives 17 and 18, respectively. Compound 17 was indirectly and 18 was directly converted to (±)‐20‐deethylvincadifformine (7) and (±)‐20‐deethyl‐20‐epivincadifformine (8). Epimerization occurred in both cases. The thioxo compound 23 was used for the synthesis of (±)‐20‐deethyltabersonine (28) and (±)‐20‐deethyl‐3‐oxotabersonine (27). Oxidative ring transformation of the (±)‐20‐deethylvincadifformine (7) gave (±)‐16‐deethylapovincamine (29).

Original languageEnglish
Pages (from-to)1245-1251
Number of pages7
JournalLiebigs Annalen
Volume1995
Issue number7
DOIs
Publication statusPublished - Jun 23 1995

Keywords

  • Alkaloids
  • Deethylapovincamine
  • Deethyltabersonine
  • Deethylvincadifformine
  • Deethyl‐3‐oxotabersonine

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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