Synthesis of Vinca Alkaloids and Related Compounds. 90.1 New Results in the Synthesis of Alkaloids with the Aspidospermane Skeleton. First Total Synthesis of (±)-3-Oxominovincine

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

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Abstract

The tryptamine derivative 1 readily reacted with methyl 4-acetyl-5-bromopent-4-enoate (9) that had been built up from 2,4-pentanedione. On intramolecular dehydration and subsequent [4 + 2] cycloaddition, the reaction product 10 gave the epimers 12 and 13 having the D-secoaspidospermane skeleton. Compound 12 directly and 13 after epimerization yielded (±)-3-oxominovincine (14). Regioselective reduction of 14 furnished (±)-minovincine (17).

Original languageEnglish
Pages (from-to)9188-9191
Number of pages4
JournalJournal of Organic Chemistry
Volume62
Issue number26
Publication statusPublished - Dec 1 1997

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ASJC Scopus subject areas

  • Organic Chemistry

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