Synthesis of Vinca Alkaloids and Related Compounds. 64. Total Syntheses of (±)-Pseudovincadifformine and (±)-20-Epipseudovincadifformine

György Kalaus, István Greiner, Mária Kajtár-Peredy, János Brlik, Lajos Szabó, Csaba Szántay

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Using our previously reported convergent synthetic strategy, secondary amine 6 and aldehyde 9 reacted to give tetracyclic esters 10 and 11, which readily led to pentacyclic lactams 14–16. Selective reduction of these products gave (±)-pseudovincadifformine (4), (±)-20-epipseudovincadifformine (5), and (±)-14-epipseudovincadifformine (20). Aldehyde 23 was also prepared and could be directly used for synthesizing (±)-20-epipseudovincadifformine (5). The introduction of the double bond into ring D of the pseudoaspidospermane skeleton was successfully achieved to obtain 21-oxopseudotabersonine (30).

Original languageEnglish
Pages (from-to)6076-6082
Number of pages7
JournalJournal of Organic Chemistry
Volume58
Issue number22
DOIs
Publication statusPublished - Jan 1 1993

ASJC Scopus subject areas

  • Organic Chemistry

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