Synthesis of vinca alkaloids and related compounds. Part 107. An efficient convergent synthetic pathway to build up the ibophyllidine skeleton III. Total synthesis of(±)-ibophyllidine and (±)-20-epiibophyllidine

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

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6 Citations (Scopus)

Abstract

Starting from 5-ethyldihydrofuran-2(3H)-one (9) we prepared aldehydes (6 and 7) which, in a [4+2] cycloaddition reactions with the tryptamine derivative (8) gave, as a final step, compounds (13 and 22) having D-seco-pseudoaspidospermane skeleton. We synthesized (±)-20-epiibophyllidine (4) via the benzoate ester (15) or the mesylate (17) of alcohol (14) which had been obtained from 13, while the catalytic hydrogenation of 22 led to (±)-ibophyllidine (3) via full epimerization, cyclization and reduction steps in one operation.

Original languageEnglish
Pages (from-to)865-880
Number of pages16
JournalHeterocycles
Volume71
Issue number4
Publication statusPublished - Apr 1 2007

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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