Synthesis of vinca alkaloids and related compounds. Part 106. An efficient convergent synthetic pathway to build up the ibophyllidine skeleton II. Total synthesis of (±)-deethylibophyllidine and (±)-14-EPI-deethylibophyllidine

Flórián Tóth, György Kalaus, István Greiner, Mária Kajtár-Peredy, Ágnes Gömöry, László Hazai, Csaba Szántay

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9 Citations (Scopus)

Abstract

Starting from 2,3-dihydrofuran (7) we prepared aldehyde (5) which, in a [4+2] cycloaddition reaction with the tryptamine derivative (4) gave, as a final step, compound (10) having a D-seco-aspidospermane skeleton. We synthesized (±)-14-epi-deethylibophyllidine (3) via the mesylate (12) of alcohol (11) which had been obtained from 10, whereas the cyclization of the benzoate ester (15) resulted in (±)-deethylibophyllidine (2). We have managed to build up (±)-2 via the tetracyclic intermediates (16) and (20).

Original languageEnglish
Pages (from-to)2301-2317
Number of pages17
JournalHeterocycles
Volume68
Issue number11
Publication statusPublished - Nov 1 2006

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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