Synthesis of Vinca Alkaloids and Related Compounds. 63. A New Synthetic Pathway for Preparing Alkaloids and Related Compounds with the Aspidosperma Skeleton. Total Syntheses of (±)-Vincadifformine, (±)-Tabersonine, and (±)-3-Oxotabersonine

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

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Abstract

Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of 2-(ethoxycarbonyl)tryptamine (2). The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (±)-vincadifformine (4), (±)-3-oxotabersonine (42), and (±)-tabersonine (43). The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tetracyclic benzoate esters 37 and 38. The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.

Original languageEnglish
Pages (from-to)1434-1442
Number of pages9
JournalJournal of Organic Chemistry
Volume58
Issue number6
DOIs
Publication statusPublished - Jan 1 1993

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ASJC Scopus subject areas

  • Organic Chemistry

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