Synthesis of vinca alkaloids and related compounds. 64. Total syntheses of (±)-pseudovincadifformine and (±)-20-epipseudovincadifformine

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

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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
Publication statusPublished - 1993

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Vinca Alkaloids
Aldehydes
Lactams
Amines
Esters

ASJC Scopus subject areas

  • Organic Chemistry

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Synthesis of vinca alkaloids and related compounds. 64. Total syntheses of (±)-pseudovincadifformine and (±)-20-epipseudovincadifformine. / Kalaus, György; Greiner, István; Kajtár-Peredy, M.; Brlik, János; Szabó, Lajos; Szántay, Csaba.

In: Journal of Organic Chemistry, Vol. 58, No. 22, 1993, p. 6076-6082.

Research output: Contribution to journalArticle

Kalaus, György ; Greiner, István ; Kajtár-Peredy, M. ; Brlik, János ; Szabó, Lajos ; Szántay, Csaba. / Synthesis of vinca alkaloids and related compounds. 64. Total syntheses of (±)-pseudovincadifformine and (±)-20-epipseudovincadifformine. In: Journal of Organic Chemistry. 1993 ; Vol. 58, No. 22. pp. 6076-6082.
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